While the Blues were bested 1-0 by Liverpool in front of the Wembley crowds on Sunday, Daniel Farke's troops rejoiced in a 3-1 beating of Championship leaders Leicester City on Friday night.
Match preview
Mauricio Pochettino's opposite number Jurgen Klopp could have put together a full XI of injured players before Sunday's EFL Cup final commenced, and with the Reds' absentee crisis worsening on the Wembley turf, the time was nigh for the Chelsea boss to finally end his English trophy hoodoo.
However, even as Klopp called upon the kids to reinforce his ravaged unit, a passive Chelsea lacked a cutting edge and were ostensibly playing for penalties as the clock ticked down in extra time, only to see Virgil van Dijk's glancing header nestle into the bottom corner to decide the destiny of the crown.
The Dutchman's contribution prolonged Pochettino's agonising wait for a first major honour in English football, one which he could still potentially snap in the FA Cup, where Chelsea thrashed Preston North End 4-0 in round one before an impressive fourth-round replay beating of Aston Villa.
Many an eyebrow was raised as the Blues played the Lions off the park at Villa Park - a ground where Unai Emery's men had been hitherto flawless - and Chelsea have progressed past the fifth round of the FA Cup six times in the last eight seasons, while winning 13 of their last 15 matches at this juncture.
The hosts' playing staff and crestfallen supporters are unlikely to have fully healed from Sunday's heartbreak by the time Leeds arrive at Stamford Bridge, where they are at risk of falling back into old habits; the Blues are winless in two straight home games after seven successive triumphs from December 3 to January 23.
Speaking of winning streaks, a sixth consecutive victory across all competitions arrived for Leeds in Friday's tantalising Championship contest with leaders Leicester City, where Farke's men reduced the gap to the Foxes to just six points under the bright lights of Elland Road.
Wout Faes's 15th-minute header propelled Leicester into a slender advantage, which the visitors would cling onto heading into the final 10 minutes, but a late Foxes capitulation saw Connor Roberts, Archie Gray and Patrick Bamford complete a stunning turnaround for the Whites.
Still building up a head of steam in their quest for an immediate return to the big time, Leeds' second-tier record in 2024 remains unblemished - nine wins from nine games have arrived since the turn of the year - and the only contest that the Whites have not won since January 1 was their initial FA Cup fourth-round showdown with Plymouth Argyle.
However, Farke's men rectified their Elland Road errors with a 4-1 extra-time crushing in torrid conditions at Home Park, thus reaching the fifth round for the second year running, but they have failed to progress further since reaching the quarter-finals of the 2002-03 edition.
The Whites have to go back even further for their most recent success over Chelsea at Stamford Bridge, which came in a December 1999 Premier League fixture, since when the Blues have earned six straight wins over their Championship counterparts at their West London home.
Chelsea FA Cup form:
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D
W
Chelsea form (all competitions):
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L
W
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D
L
Leeds United FA Cup form:
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D
W
Leeds United form (all competitions):
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W
Team News
While Liverpool left Wembley much worse for wear - albeit with winners' medals around their necks to boot - Chelsea did not pick up any fresh injury concerns in the EFL Cup final, although Thiago Silva's groin issue did not heal in time for the 39-year-old to be involved.
Whether Silva is fit enough to marshal the backline on Wednesday only time will tell - Marc Cucurella (ankle) is in the same boat - but Wesley Fofana (knee), Reece James (thigh), Lesley Ugochukwu (thigh), Romeo Lavia (thigh), Carney Chukwuemeka (ankle) and Benoit Badiashile (groin) remain unavailable.
However, Robert Sanchez was back in the matchday squad at Wembley and could be one of several players to benefit from the tight turnaround, a list which also comprises Trevoh Chalobah, Alfie Gilchrist, Noni Madueke, Christopher Nkunku and Mykhaylo Mudryk.
Leeds can empathise with Chelsea on the defensive injuries front, as all of Karl Darlow (finger), Pascal Struijk (groin), Sam Byram (leg) and Stuart Dallas (hip) are confined to the treatment room and will play no part in the fifth-round tie.
The visitors came through Friday's game unscathed, though, and Farke will have Burnley loanee Roberts at his disposal for the fifth round; the right-back could not take part in the replay versus Plymouth on account of not being registered for the original fixture.
Both Roberts and Bamford have thrown their hat into the ring for starts at Stamford Bridge thanks to their roles in a stellar Whites fightback versus Leicester, while Ethan Ampadu should be given the nod from the off against his former employers.
Chelsea possible starting lineup:
Sanchez; Gusto, Gilchrist, Chalobah, Colwill; Gallagher, Fernandez; Madueke, Nkunku, Mudryk; Sterling
Leeds United possible starting lineup:
Meslier; Roberts, Ampadu, Cooper, Firpo; Gruev, Kamara; Gnonto, Rutter, Anthony; Bamford
We say: Chelsea 2-1 Leeds United
As well as finding the back of the net for fun, Leeds have also prided themselves on a rigid defensive structure in 2024; Faes's opener for Leicester on Friday was just the fourth goal that they have conceded in their 12-game unbeaten run.