Tottenham saw their title hopes all but end with a surprise defeat to Burnley and the Blues lost to Manchester City on penalties in the EFL Cup final, possibly leaving Maurizio Sarri with this one game to save his job.
The big talking point to come out of Chelsea's spot-kicks heartbreak in Sunday's clash at Wembley, following 120 goalless minutes, was Kepa Arrizabalaga's refusal to leave the field when Sarri tried to sub him late on.
Sarri was undermined by his goalkeeper and his mood would not have improved over the next 15 minutes as his side lost 4-3 on pens. The under-fire Italian was reportedly given the EFL Cup final and Wednesday's visit of Tottenham to show that he deserves to remain in charge; make that just one match.
Defeat at Stamford Bridge on Wednesday and Chelsea may well go the same route as top-four rivals Manchester United in sacking their manager and appointing a caretaker boss. England assistant manager Steve Holland's name has been mentioned, having spent eight years working in various roles at the club prior to his switch to the Three Lions' camp.
Sarri will point out the fine margins between success and failure, which is never clearer than when a cup final is decided on penalties, but the bottom line is that Chelsea have now tasted defeat in two cup competition in the space of a week, with Sunday's EFL Cup heartbreak coming six days on from the 2-0 FA Cup fifth-round reverse at the hands of Man United.
The Blues do at least still have the Europa League to aim for and they are in contention for a top-four finish in the Premier League, even if they have slipped down to sixth place. Arsenal occupy the final Champions League qualification berth, though Chelsea are within three points of their London rivals and have a game in hand to play.
With Arsenal putting together back-to-back wins and United still unbeaten in 13 domestic matches under Ole Gunnar Solskjaer, Chelsea know that they cannot afford to continue stuttering in the top flight. In their last four league matches, Sarri's side have won one and lost three, conceding 12 goals and scoring none across those three losses.
The 6-0 thrashing away to Man City is still fresh in the memory, as are the 2-0 and 4-0 defeats to Arsenal and Bournemouth respectively. All three of those losses came away from home, though, and the West Londoners have a far better home record, losing just one of their last 15 league matches at Stamford Bridge - 1-0 to Leicester City just before Christmas.
Chelsea's failure to score in three of their last four Premier League games will be a massive concern for Sarri, and they were also unable to find a way through in the cup matches against the Manchester duo. Another blank on Wednesday and Roman Abramovich may well decide that enough is enough.
Recent form in Premier League: DWLLWL
Recent form (all competitions): WLWLWL
Not for the first time in recent years, just when Tottenham's title hopes were being talked up they hit a brick wall in suffering a 2-1 defeat at Burnley in Saturday's early kickoff. On a weekend when Liverpool had a tough trip to Man United, Spurs were unable to assert any pressure as they came unstuck to goals from Chris Wood and Ashley Barnes.
Mauricio Pochettino was furious with some of the decisions made by the officials, but his side were below-par and did not deserve to come away from Turf Moor with maximum points. Pochettino squared up to referee Mike Dean at full time and is now facing a hefty punishment and possible touchline ban.
The Argentine admitted at his post-match press conference that he let his emotions get the better of him after seeing his side, who had collected 12 points from the last 12 on offer heading into the match, pass up the chance to claw themselves to within two points of the division's top two.
Instead, Tottenham are now six points adrift of Liverpool and their title hopes are surely over for another year, unless both Man City and Liverpool hit a bad patch of form between now and the end of May.
Tottenham need to ensure that they are well positioned to pounce if that does happen, and three points on enemy territory on Wednesday would be the perfect way to send out a message to their critics. Defeat, though, and all of a sudden they may well be looking over their shoulder at the chasing pack in pursuit behind them.
The Lilywhites will fancy their chances of picking up a midweek victory, however, as only Arsenal (16 in eight games) have won more points in Premier League London derbies this season than themselves (15 in six games).
One of those derby victories came in the reverse fixture, as goals from Dele Alli, Harry Kane and Son Heung-min inflicted a first defeat on Sarri's Chelsea, but not since 1970-71 have they won both league games against Chelsea in a single season.
With Arsenal up next and a trip to Borussia Dortmund to follow close behind, now is not the time for Tottenham to feel sorry for themselves. A response is needed at Stamford Bridge and a victory may just give their outside title ambitions a welcome shot in the arm.
Recent form in Premier League: LWWWWL
Recent form (all competitions): LWWWWL
The one positive to come out of Tottenham's defeat in Lancashire was the goalscoring return to action of Kane. The England striker was not expected to return for another couple of weeks, but he hit the ground running at Turf Moor and should retain his place up top against Chelsea.
Eric Dier was absent at the weekend because of illness, though, while Kieran Trippier and Davinson Sanchez were left out of the squad entirely, so all three players could possibly be recalled on Wednesday.
There is still no Alli for Tottenham, but Pochettino's injury list has otherwise cleared up at a crucial period in the season.
Christian Eriksen is a certain starter for Spurs, meanwhile, and he has been involved in 15 goals in 17 Premier League games played on a Wednesday (seven goals, eight assists), including two assists against Chelsea in January 2017.
In terms of the home side, Sarri must decide whether to stick with Kepa in goal or bring in Willy Caballero following his "misunderstanding" with the world's most expensive keeper at Wembley.
Elsewhere, Marcos Alonso was not used against Man City and will be fully fit for this match, and there is also expected to be some rotation in the forward line as Callum Hudson-Odoi and Gonzalo Higuain are pushing for inclusion.
Chelsea possible starting lineup:
Kepa; Azpilicueta, Rudiger, Luiz, Alonso; Kante, Jorginho, Kovacic; Hudson-Odoi, Higuain, Hazard
Tottenham Hotspur possible starting lineup:
Lloris; Alderweireld, Sanchez, Vertonghen; Trippier, Sissoko, Winks, Davies; Eriksen; Kane, Son
Head To Head
Chelsea have only lost one of their last 32 home games against Tottenham in all competitions, though that defeat did come in this corresponding fixture last season.
Spurs have won three of their last four top-flight encounters with the Blues - as many as they had managed in their previous 20 against them.
Not since between March 1961 and September 1963 have Tottenham won three consecutive league matches against Chelsea, which they can achieve with victory on Wednesday.
However, Chelsea knocked Tottenham out of the EFL Cup at the semi-finals stage last month thanks to a comeback win over a two-legged tie that was settled by penalties.
We say: Chelsea 1-2 Tottenham Hotspur
Both teams need to quickly pick themselves up following disappointing results at the weekend. Pochettino has won four Premier League games against Chelsea as Tottenham boss - more than every other Spurs manager combined in the competition - and his side have been far more consistent than their opponents over the course of the season. Just when they have been written off once again, the Lilywhites could well drag themselves right back into the title picture in the midweek round of fixtures.