Croatia last graced this stage in 1998 and are bidding to reach their first ever World Cup final, whereas England have not made it to the biggest game in football since lifting the trophy for the one and only time in 1966.
Croatia came into this summer's World Cup boasting some of the most talented players at the tournament, but their recent record on the biggest stage left them quite far down the list of potential winners.
Since finishing third in 1998 - their first World Cup as an independent nation - Croatia have failed to make it past the group stages, and even missed out on qualification altogether in 2010.
However, the likes of Luka Modric, Ivan Rakitic and Mario Mandzukic have finally come good this summer and, in what may be the trio's final World Cup, they now stand on the brink of the greatest achievement in their nation's footballing history.
While Croatia may not be able to match the World Cup pedigree of even England, their squad does boast significant experience and at club level they have won nine Champions League titles between them. England's players, by contrast, have won just one.
Not even a Champions League final can quite prepare someone for the pressure of a World Cup semi-final, though, and so far Croatia have struggled slightly in the knockout stages of the tournament.
After cruising through Group D with a 100% record - including a 3-0 win over Argentina - Croatia have needed penalties to scrape past Denmark in the last 16 and then host nation Russia in the quarter-finals.
England should pose more of threat than those two previous knockout opponents, but Croatia have certainly shown character during those past two games; they bounced back from a first-minute goal against Denmark and then picked themselves up after a 115th-minute Russian equaliser to win on penalties.
Only one other nation has ever won two penalty shootouts at a single World Cup - Argentina doing so in 1990 - and fatigue could play a part should Wednesday's match also look like going the distance.
Croatia do have a good record against European opposition at the World Cup, though, with the 1998 semi-final defeat to France their only loss in eight such matches. Indeed, that loss to the hosts 20 years ago is also their only defeat in six previous World Cup knockout games.
There are also goals throughout this Croatia team, with their 10 World Cup goals being scored by eight different players - a tally second only to fellow semi-finalists Belgium.
Whether that is an advantage compared to having one particularly prolific goalscorer like England's Harry Kane remains to be seen on Wednesday night, but manager Zlatko Dalic is confident that his side can stop the Three Lions captain and, if they do, they could well be on course for a historic World Cup final appearance.
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World Cup fever has well and truly gripped the nation and fans, players and pundits alike will have been wishing for Wednesday night to come around from the moment the final whistle went in the quarter-final win over Sweden on Saturday.
The semi-final against Croatia will be the biggest match in English football for 28 years, since they last reached the semi-finals at Italia '90. Indeed, some may argue that it is the biggest game since the 1966 final considering how the draw has opened up for them.
There has been semi-final heartbreak for England in the past, though, from Gazza's tears in 1990 to current manager Gareth Southgate missing the crucial penalty in the last four of Euro '96, so fans will still be guarded despite the team already surpassing all expectations in Russia.
It is perhaps no coincidence that a tournament which began with almost unprecedentedly low levels of expectation has resulted in England's best run for almost three decades, with the players finally looking free from what has been a suffocating weight of pressure in the past.
Some old demons have been exorcised too; a first World Cup penalty shootout victory in four attempts over Colombia in the last 16 saw belief levels shoot up, and the relatively comfortable nature of their 2-0 win over Sweden in the quarter-finals - albeit via a man-of-the-match display from goalkeeper Jordan Pickford - instilled further confidence in the ability of Southgate's youthful squad to handle the big occasion.
There is no getting away from the fact that the draw has fallen kindly for England, though, and Croatia are likely to be a step up in class from any other team they have faced in Russia so far given that their final group game against Belgium saw Roberto Martinez field a second-string side.
One route to success for England could be via set pieces, which have proven to be a rich source of goals for them at this World Cup. Eight of their 11 goals have come via that route - already the most at a World Cup since Portugal in 1966 - while three of the four goals Croatia have conceded have also come from set pieces.
Fans will take any omens that grant optimism at this stage of a tournament too, and the last three teams to score four or more goals from corners at a World Cup - a feat England have already achieved - have gone on to lift the trophy; Germany in 2014, Italy in 2006 and France in 1998.
Regardless of what happens on Wednesday night, it has already been a World Cup to remember for England; their tally of 11 goals is their joint-highest ever - alongside 1966 - and they have come from five different goalscorers, which is also the joint-most they have ever had at a tournament.
Southgate's side will arrive in Moscow full of confidence having lost just two of their last 30 competitive games and only one of their last six World Cup outings, although if they are to progress then they will have to beat two European nations at a single World Cup for the first time since 1982.
The Three Lions have already broken records galore at this tournament, though, and if they can end the semi-final hoodoo which has seen England lose their last three at major tournaments then they will etch their names even deeper into English football history.
One month ago it would have been scarcely believable that England would still be involved in the final week of the World Cup, but the Three Lions are potentially now just 180 minutes away from bringing it home.
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Southgate should have a fully fit squad to choose from for Wednesday's match after all 23 players took part in their final training session on Tuesday morning.
Jordan Henderson - who is on an unprecedented run of 30 consecutive England games unbeaten - had been a doubt with a tight hamstring, but he is expected to be fit to play.
There were also minor doubts over the fitness of Pickford and Dele Alli, but both are also expected to feature with Southgate likely to name an unchanged side.
Should that be the case then Raheem Sterling will once again lead the line alongside Kane, despite criticism of his performance during the win over Sweden.
Kane has had no such trouble in front of goal and still leads the Golden Boot race with six goals - a tally only Ronaldo in 2002 has bettered from the past nine World Cups and one no European player has beaten since 1974.
Jamie Vardy is back available after missing the quarter-final win over Sweden with a groin problem, but he is likely to be left on the bench once again.
Dalic is also sweating over the fitness of goalkeeper Danijel Subasic, who picked up a hamstring injury against Russia but went on to finish the match.
Croatia possible starting lineup:
Subasic; Vida, Lovren, Corluka, Strinic; Rakitic, Brozovic, Rebic, Modric, Perisic; Mandzukic
England possible starting lineup:
Pickford; Walker, Stones, Maguire; Henderson; Trippier, Lingard, Alli, Young; Sterling, Kane
Head To Head
This will be the eighth meeting between these two sides, with England winning four and losing two of the previous seven.
One of those England victories came in their only previous meeting at a major tournament, with a teenage Wayne Rooney helping England to a 4-2 victory in the group stages at Euro 2004.
Croatia got revenge with a victory over Steve McClaren's England which denied them a place at Euro 2008, although the last two meetings have seen England win by a 9-2 aggregate scoreline - winning 4-1 in September 2008 before sealing their place at the 2010 World Cup with a 5-1 triumph at Wembley.
We say: Croatia 1-2 England (a.e.t)
Croatia have not been at their best in the knockout rounds so far, and they could be forced to go all the way again on Wednesday, which could give England's slightly fresher legs the edge. It promises to be a hard-fought encounter, but we're backing England to make it into the final.