The visitors took the lead just before the hour mark when Ikechi Anya marked his full debut with his first goal for his country, latching on to a Barry Bannan pass before drilling his shot across the keeper and into the far corner.
Shaun Maloney guided an inch-perfect free-kick over the wall and into the top corner in the 89th minute to ensure that his side left Skopje with all three points.
You can read how an entertaining 90 minutes of international football unfolded with Sports Mole's live coverage below.
6.30pmGood evening! Thank you for joining Sports Mole for tonight's World Cup qualifying Group A match between Macedonia and Scotland as both sides look to avoid finishing bottom of the pile. Let's get straight down to business, shall we?
6.32pmLet's start by looking at our hosts tonight, and Macedonia will be hoping that Scotland's trip to Skopje will not end with fond memories. Cedomir Janevski's side will come into this match full of confidence having hit a decent spell of form recently.
6.34pmMacedonia have won their last two matches including friendlies, matching their best spell of form for over three years. The last time that they won more than two matches in a row came when they beat Montenegro, Azerbaijan and Romania in succession back in 2010.
6.36pmTheir last outing saw them come up against Group A's other British representatives as Wales - complete with Gareth Bale as an unused substitute - failed to come away from Skopje with anything. The brilliantly-named duo of Trickovski and Trajkovski both got their names on the scoresheet as Macedonia ran out 2-1 winners to lift themselves off the bottom of the group.
6.38pmBefore Friday's victory over Wales, Macedonia's last match saw them run out 2-0 victors over Bulgaria in a friendly last month. However, if we are to stretch a little further back, before this two-game winning streak - if it can be considered a 'streak' yet - Macedonia lost four matches on the trot, all without scoring a single goal.
6.40pmIn fairness to Macedonia, two of those games were friendly matches against Sweden and Norway, both teams significantly higher than Macedonia in the FIFA World rankings. The other two were also against a team they were not expected to beat as Group A leaders Belgium won both legs of a double-header back in March.
6.42pmSpeaking of FIFA Rankings, Macedonia come into this match ranked 89th in the world. That is actually an improvement on their placing from last month, although they are still behind the likes of the Central African Republic. The FIFA rankings do have to be taken with a pinch of salt, but they are rarely so wrong that Macedonia's place isn't completely unwarranted.
6.44pmMacedonia come into this match now sitting fourth in Group A following Friday's result against Wales, which saw them leapfrog both their opponents on that night and their opponents tonight. They have won two, drawn one and lost four of their seven matches, amassing seven points.
6.46pmThey began their qualifying campaign with a 1-0 loss to Croatia before their first point came almost exactly a year ago to the day with a 1-1 draw against Scotland. They then lost 2-1 to Croatia before something of a surprise 1-0 win over Serbia. There was nothing surprising about their back-to-back defeats against Belgium, but Macedonia have proved a hard team to beat throughout this qualifying campaign. Only Belgium have beaten them by more than one goal (2-0).
6.48pmThe hosts could move as high as third with a win this evening, depending on results elsewhere (namely Serbia's clash with Wales). However, on the flip side, they could be banished back to the foot of the table with a defeat, again depending on whether Wales can get anything out of Serbia.
6.50pmMoving on to Scotland, and there is a growing sense that they are moving in the right direction under Gordon Strachan. There is optimism around the fans, players and coach despite coming into this match rock bottom of their qualifying group having only managed one win from the campaign so far.
6.52pmThat sense of optimism may not strictly be in keeping with current results. Their last outing saw them beaten 2-0 by Belgium, while they lost to the 'auld enemy' England 3-2 in the match preceding that. However, there were positives to take from both results for the Scots.
6.54pmAgainst Belgium, they held a very good side to 1-0 for the majority of the match, with Everton's Kevin Mirallas only adding the second goal late on. There was not much to talk about in an attacking sense - Scotland didn't have a single shot on target despite being at home - but defensively they looked strong and stubborn.
6.56pmThe highlight of the Strachan era so far undoubtedly came back in June when Scotland picked up their solitary win. Robert Snodgrass scored the only goal of the game as the Tartan Army beat Croatia 1-0 away from home. Overall, including friendlies, Strachan has won two and lost four since taking over at the helm in January, but his losing record does not tell the full story as he looks to build a team capable of challenging for the 2016 European Championships.
6.58pmUnder Strachan, and before him Craig Levein, Scotland have amassed just five points from their eight matches. That puts them just one point behind Wales and two behind Macedonia, but the Scots have played an extra game.
7pmThey began their qualifying campaign with back-to-back draws against Serbia (0-0) and Macedonia (1-1) respectively before falling to their first defeat at the hands of Wales. That was the beginning of a four-match losing streak that also saw them fall to Belgium, Wales (again) and Serbia (again) before finally breaking their duck against Croatia.
7.02pmA win tonight could lift Scotland as high as fourth in the group so long as Wales fail to beat Serbia, but a loss could potentially leave them cast four points clear at the bottom. With this being their penultimate game, that would seal their fate in Group A.
7.04pmTEAM NEWS: Right then, it is time for some team news! The biggest news comes from the Scotland camp as Watford's Ikechi Amenya makes his full debut for his country, while Barry Bannan and Steven Naismith also come into the side. For Macedonia, meanwhile, Goran Pandev has shaken off a fitness concern and will start.
7.10pmSo, what can we expect from those two teams? Well, from Macedonia's point of view, their main threat will be Goran Pandev. The experienced striker is their top goalscorer of all time, and actually has more international goals to his name than the entire Scotland team combined.
7.12pmAs for Scotland, Leigh Griffiths barely saw any of the ball against Belgium and, as such, is replaced by Naismith. Barry Bannan, meanwhile, comes in for James Forrest but most eyes will be on Anya tonight.
7.14pmThe Watford man came on as a sub against Belgium and looked sharp. It was a very tough game for any Scottish players to shine in as far as attacking is concerned, but he made one break down the left that was just about as threatening as Scotland looked all night. It will be interesting to see how he performs tonight, coming in for the suspended Robert Snodgrass.
7.16pmIt will also be interesting to see how Strachan approaches this match tonight. Steven Naismith is not what I would describe as an 'out and out striker', but he is likely to be the furthest forward for Scotland tonight. They could well feel the absence of Jordan Rhodes, who was forced to pull out of the squad with a hand injury.
7.18pmStrachan has admitted that he is "scared" of finishing bottom of the group, and he may have good reason to. For all Scotland have had trouble reaching major tournaments in recent years, they have only ever finished bottom of their qualifying group once. This current crop of players will be as desperate as their manager not to associate their names with doubling that tally.
7.20pmPREDICTION: Right, we are 10 minutes from kickoff in Skopje, which means that it is time for a prediction! It is fair to say that these sides are not two of football's powerhouses, so I am not expecting a footballing clinic by any means. With the emphasis on avoiding finishing bottom of the group we could be in line for a defensive match, and I think both teams could cancel each other out. I'm going to go for a 1-1 draw.
7.22pmThat 1-1 draw would be a repeat of the scoreline the last time these two teams met, almost a year to the day ago. Kenny Miller scored for the Scots on that occasion, but they won't be able to call upon him today after the striker retired following their 3-2 defeat to England.
7.24pmMacedonia did win the last time these two teams met in Macedonia. That was five years ago - again, almost to the day - when Scotland fell to a 1-0 defeat during qualifying for the 2010 World Cup.
7.26pmOverall, these two teams have met just the three times, and it is a nice and balanced record going into the fourth encounter. Each side has won one apiece with one draw, but Scotland edge it in terms of goals having scored three to Macedonia's two.
7.28pmA total of 39 places separate these two teams in the FIFA rankings, with Scotland going in to this match with the advantage according to that table. The visitors are listed as the 50th best national team in the world, while I have already mentioned that Macedonia are ranked 89th.
7.30pmSo, for all of the talk of progress amongst the Scotland camp, they haven't really backed it up with results other than that impressive Croatia win. Tonight would be a great time to start doing so.
1 minKICKOFF: Here we go then, Scotland get us underway in a match that has plenty of pride of stake for both sides. Defeat for Scotland could see them consigned to bottom place in the group.
3 minBright start from the visitors as they immediately take control of the ball and look to make things happen early on. I said before the match that this could be a cautious affair, but Scotland haven't started in that way.
4 minImportant piece of tracking back from Anya there. Georgievski was racing down the right flank looking to get on the end of Babunski's pass, but Anya was there to intercept and run it out for a corner.
6 minEven this early in the match, it is clear that the conditions could play a big part tonight. It is hot in the stadium but, more worryingly for Scotland, the pitch is already starting to cut up.
8 minUPDATE: I will keep you updated with tonight's matches involving home nations this evening, with a particularly close eye on the other match in this group as Wales host Serbia. First to score from the home nations, though, are Northern Ireland, who have taken a 1-0 lead against Luxembourg.
10 minAnya has made a bright start to this match down the left flank. He looks eager to take on his man at every opportunity and he injects pace into the Scotland attacking that was severely lacking against Belgium.
12 minAnya really has been involved in the game a lot too. His teammates seem to have recognised his eagerness to impress on his full debut, and they are giving him the ball at every available opportunity.
12 minHutton bursts down the right flank before being taken down by Ristovski. Bannan has a good chance to swing the ball in from a promising position, but his delivery is too close to the keeper and is comfortably collected. That was a waste.
14 minAnother waste of a good position for Scotland. The visitors again attack down the left flank and Anya gives the ball to the overlapping Whittaker, but his cross is poor and allows Macedonia to launch a counter attack.
15 minThere is perhaps the first example of Scotland's lack of a true striker today. Anya sends a cross into the box that bounces pretty close to the penalty spot, but no white shirts are attacking it and eventually the attacker fades away.
17 minMacedonia have a defender taking their goal kicks at the moment. I'm not sure whether the keeper is injured or just doesn't have a big enough boot on him but, if it's the latter, it is always good to see elements of Sunday league football finding their ways to this level!
19 minPlenty of decent build-up play from Scotland at the moment, but no real threat in the final third so far. That is perfectly summed up by an effort from Charlie Mulgrew there. A number of players were involved in a slick move, but the Celtic man's shot went a long, long way over the top.
21 minNothing to report in terms of chances from either side in the opening 20 minutes. Anya has looked the brightest player on the park so far, but not even he has been able to create a spark of magic yet.
22 minMaloney sends a free kick into a good area but, not for the first time tonight, the ball bounces into the box without a Scottish player attacking it. They need to take a few more risks in those situations.
24 minThe fans are beginning to get a bit restless already. Neither side have created anything for them to cheer so far, and the home fans in particular are not happy with the lack of urgency in their build-up play.
25 minAnya again makes progress down the left flank but again there is nobody in the box to attack his cross. Yes, the winger's cross wasn't perfect, but he really didn't have many choices in the middle there.
26 minCHANCE! It's not exactly a golden chance, but it is the clearest sight of goal we have had so far. Unsurprisingly, Anya is the man who creates it as he swings a cross into the middle of the box which Naismith heads over from the middle of the box.
27 minAnya is giving Georgievski a torrid time on the left wing at the moment. Yet again he beats his man before pulling the ball back along the floor, but this time it falls just behind Naismith. Good, direct running once again from the Watford winger.
28 minSHOT! Hanley gets up well to reach a corner, but his downward header goes a couple of yards wide. Again, not the best chance but a decent enough sight of goal for the visitors.
30 minUPDATE: Good news for Scotland as Serbia have taken the lead against Wales in Cardiff. That means that, as things stand, Scotland will be level on points with Chris Coleman's men at the bottom of Group A.
32 minCHANCE! By far the best chance of the match so far falls Scotland's way, and it really should be 1-0. One lofted through ball beats the entire Macedonian defence and Craig Brown suddenly finds himself clean through on goal with only the keeper to beat. The skipper never really looks comfortable with the chance, however, and his tame effort is saved by Pacovski.
34 minUPDATE: Those minnows of Luxembourg have levelled the sides against Northern Ireland. It is now 1-1 in that match.
36 minWe haven't seen much from Goran Pandev so far but, then again, he hasn't been given the chance to showcase his talents. No matter how good you are - and there is no doubting the Napoli striker's quality - you are going to struggle when you are this isolated.
38 minThe only things that Marshall has had to do so far today is pluck a few over-hit crosses out of the air. It has been pretty much another spectator for today's match so far as Macedonia struggle to create anything of note in the Scotland half.
40 minThat is a little better from Macedonia as they string a few passes together for the first time tonight. Georgievski finally gets a break from marking Anya as he ploughs forward down the right flank, but his cross is cleared by Hanley.
42 minMACEDONIA SUB: This is a rather strange sub from Macedonia. Just before half time, off comes 19-year-old Babunski to be replaced Tasevski. I'd assume that the youngster is injured, but he jogs off the field happily enough and immediately goes to the bench rather than the dressing room. Odd one.
44 minSAVE! Pacovski is called into action for the second time tonight as Anya tries to curl an early effort into the top corner with his right foot. He doesn't get it wide enough, however, and the Macedonia keeper it able to reach up and push the ball away with one hand.
45 minCHANCE! Macedonia break from the resulting corner and create their first chance of the match. It was Jahovic who was slipped in down the left side of the area, but he couldn't keep his composure and sliced his shot into the side netting. That would have been very much against the run of play!
45 minThere will be one minute of added time at the end of this half.
8.20pmThe referee brings the first half to an end, and it was one which held plenty of positives for Scotland, but also some age-old frustrations. They have dominated possession and look in complete control of the match, but they have struggled to turn that into chances and have rarely looked like scoring.
8.22pmCraig Brown had the best chance of the match when he was released by a lofted through ball, but he couldn't bury his one-on-one opportunity. It was decent goalkeeping from Pacovski, but Brown didn't make it anywhere as hard for the Macedonia keeper as it should have been, and he really ought to have scored.
8.24pmSteven Naismith has also had a decent sight of goal for the visitors, but he failed to keep his header down having been found by Anya. It wasn't quite as good an opening as Brown's, but with Scotland struggling to create many clear opportunities they need to start taking any half-chances that come their way.
8.26pmFor all of Scotland's dominance, they almost went into the break behind when Macedonia launched a counter attack just before half time. Jahovic got into a very good position for the hosts, but he lacked composure and shanked his shot into the side netting when he should have done better. It would have been harsh on Scotland, but they know that the longer this stays at 0-0 then the more chance Macedonia have of nicking it.
8.28pmThe man of the half was undoubtedly Scotland's full debutant Ikechi Anya. The winger gave his full-back a torrid time throughout, making it to the byline time after time and putting crosses into the box that no Scotland striker seems to want to attack. He has also had a good shot of his own saved, and looks to be the most likely route to a goal this evening.
8.30pmUPDATE: The other match in this group kicked off slightly later tonight and, as such, is still in action while we're in half time. Serbia have just doubled their lead over Wales, which would give Scotland a chance to move off the bottom of Group A with a win tonight.
46 minKICKOFF: Well, that is a new one for me! The referee blows for the start of the half and Macedonia duly kick off before seeing their own goalkeeper jogging onto the field late! The referee pulls it back and restarts the match again - that could have been embarrassing all round!
46 minSCOTLAND SUB: Speaking of goalkeepers coming onto the pitch, Scotland have made a change at half time bringing on Matt Gilks for David Marshall. Again, I can only assume that that is down to an injury.
48 minMaloney appears to have moved a little further forward in the early stages of this second half, which is a wise move from Strachan. The Wigan man is arguably Scotland's most creative player, so getting him in the final third more often should result in more chances for the visitors.
50 minThere is a hint of an ironic cheer from the home fans as Georgievski gets the better of Anya for once, sliding in to rob the Watford winger of the ball when he was making another enterprising run down the left.
52 minTasevski tries a clever reverse pass towards Jahovic, but the striker is not on the same page as the sub and it rolls harmlessly through to the keeper.
54 minMacedonia have their best spell of the match, but that isn't exactly saying much. They have two attacks in quick succession, but both break down through wayward passes and Scotland have a chance to clear their lines.
56 minWe're just hearing now that Marshall went off at the break with a hip injury. That is a strange injury as the Scotland keeper was not involved in any contact during the first half and had very little to do all round. Perhaps it happened when he was going to ground for Jahovic's chance at the end of the half.
57 minMACEDONIA SUB: A straight swap up front for Macedonia as they look to build upon their increased attacking threat in this second half. Trajkovski is the man who makes way to be replaced by Mirko Ivanovski.
58 minSHOT! Anya cuts inside on to his right foot, but then shows exactly why that is considered to be his weaker foot by curling his effort well over the bar.
59 minWe have the opening goal, and it just had to be Ikechi Anya who got it! The winger is released by a fine pass from Bannan and suddenly finds himself one-on-one with the keeper. His angle is quite tight, but he squeezes it across the keeper and just inside the far post. Very smart finish from the best player on the park so far today.
61 minJust before that goal, Pandev showed a small glimpse of his talent when he escaped the Scottish defence for the first time this evening. He opted against a hot from the edge of the box, instead passing it to Jahovic, who was tackled. The ball fell out to Ivanovski, who blazed one of the worst shots I have ever seen high and wide.
63 minThat goal seems to have brought Macedonia out of their shells here. For the first time tonight the hosts only had one outfield player in their own half just then, and Scotland could find that more opportunities arise as Macedonia look to get back into this one.
65 minUPDATE: Scotland's good news is not being shared by the other home nations at the moment. Northern Ireland have just fallen behind against Luxenbourg, while Wales remain 2-0 down to Serbia. England and Ireland, meanwhile, remain goalless against Ukraine and Austria respectively.
67 minYELLOW CARD! Charlie Mulgrew slides into a hard and heavy tackle on Trickovski and is subsequently handed the first yellow card of the match. He can't really have any complaints with that one.
68 minUPDATE: Better news coming out of Luxembourg for Northern Ireland - they have equalised! It is now 2-2 between those two sides with just under 10 minutes remaining.
69 min'Flower of Scotland' is ringing out from the away fans now, who are really making themselves heard for the first time today. They would love another goal to make those chants even louder and reward their dedication for travelling out to see this match.
70 minCHANCE! Big chance for Macedonia to level the sides! Trickovski is found by an incisive through ball but his first touch just lets him down a little as he is forced to hold his run which allows the defence to get back. He still manages to wrap his foot around the ball and get a shot away, but Gilks is down well to make the save and then collect before Pandev can tap in the rebound.
72 minYELLOW CARDS! Stjepanovic becomes the second player in the book for a foul on Maloney, and he is quickly followed by Whittaker, who is shown a yellow for time wasting from the subsequent free kick. That will mean that Whittaker misses the next match through suspension.
73 minSAVE! Great save from Gilks! Macedonia are getting closer and closer here, and they are needing their sub keeper to keep them ahead. Pandev slipped the ball to Ivanovski, who connected with his shot sweetly only for Gilks to tip it wide.
75 minSAVE! Gilks is called into action yet again. The ball falls to Tasevski on the edge of the box after a clumsy challenge on Pandev by Brown, but his curling effort is saved by Gilks at the near post.
76 minYELLOW CARD! Any'a nigh-on perfect evening is tarred a little by a yellow card for kicking the ball away. He went for goal having been flagged offside, so that is quite a harsh booking.
78 minCLOSE! That is just a foot or so away from Scotland doubling their lead against the run of play! Maloney gets the ball on the edge of the box and drills a low shot towards the bottom corner, but it skims narrowly wide with the keeper beaten.
79 minSCOTLAND SUB: Wigan's James McArthut joins club teammate Maloney on the field as he replaces Barry Bannan, who set up the only goal of the game so far.
80 minSCOTLAND SUB: Another change follows swiftly as Lee Wallace of Rangers replaces Whittaker. Whittaker has just been ruled out of Scotland's next match through suspension, which could have had an impact on Strachan's decision.
82 minMACEDONIA SUB:Jovan Kostovski is the latest new face to take to the field as he replaces Jahovic. The departing player may not have fond memories of tonight having missed arguably their best chance of the match just before half time.
84 minWhat an introduction for Kostovski! He has only been on the pitch for a matter of minutes and he has got his first goal for his country. Pandev was the real influence behind the goal, lifting a delicate pass over the defence to the sub, whose first touch took it away from the keeper before bundling it over the line. It wasn't the prettiest of finishes, but he won't care one bit.
86 minWell, I must say that that goal had been coming for the last 15 minutes or so. Macedonia really turned up the pressure when they went behind and, while Scotland have had the better of the game overall, Macedonia have created as many chances since going behind as Scotland have managed in the whole match.
88 minYELLOW CARD! This is a chance for Scotland, though. McArthur is brought down right on the edge of the box, and Sikov is show a yellow for his cynical foul.
89 minWell, if that proves to be the winning goal then it is a worthy one! Maloney lines up the free kick from 25 yards out and gets up up over the wall and then back down again brilliantly. It is right in the corner and the keeper has no chance. Superb strike from the Wigan man, and it makes you wonder how that is his first Scotland goal in more than six years!
90 minThere will be three additional minutes at the end of this match. Will we have any more late drama?
90+2 minIt looked as if Scotland had thrown away a win with Kostovski's late goal, but Maloney now looks to have wrestled the three points back for Scotland. This will take them off the bottom of the group as Wales are now 3-0 down to Serbia.
90+3 minCHANCE! Almost the icing on the cake for Scotland as Wallace makes a late surge forward before flashing a shot just past the far post. At the very least, that should have wasted what little remaining time we have.
9.25pmWell, things are certainly looking better for Scotland now! That late win takes them off the bottom of the table as they leapfrog Macedonia and - barring a miraculous late comeback from them - Wales to move into fourth in Group A. It was a good, confident performance on the whole from the Scots, and Gordon Strachan will be delighted with the win.
9.27pmScotland dominated the first half, but most of the action was confined to the second as Ikechi Anya - who was comfortably the man of the match this evening - scored his first goal for his country just before the hour mark. Macedonia hit back with just over five minutes left through Jovan Kostovski, who scored moments after coming on but it was the visitors who were to have the last laugh as Shaun Maloney scored a fabulous free kick to hand them all three points.
9.30pmRight, that is just about it from me tonight. Thank you for joining Sports Mole for what turned out to be a very successful night for Scotland as they picked up just their second win of the qualifying campaign courtesy of a 2-1 victory over Macedonia. I will leave you with our match report, and if you fancy a little more live football you can catch the closing stages of Ukraine vs. England, Austria vs. Ireland and Wales vs. Serbia (plus a few more games) here. From me, though, it is goodbye!