Sunday's defeat to Manchester City has left Blues' interim boss Rafael Benitez facing a scrap to secure a top-four berth, with Tottenham and Arsenal both capable of nudging Chelsea out.
Yet their hopes of silverware rest on the FA Cup and Europa League.
Benitez has already spoken about the tough run of matches his side have been facing, which has already involved a bit of juggling as their FA Cup fourth round replay with Brentford needed to be played on fifth-round weekend.
As the FA have ordered all quarter-final matches to take place on the planned weekend, it means the Middlesbrough tie must be decided in time for the winners to take on Manchester United at Old Trafford on March 10.
As Chelsea face a trip to Steaua Bucharest in the Europa League on March 7, the only available date for any replay with Middlesbrough is next Monday, March 4, just two days after a Premier League encounter with West Brom at Stamford Bridge.
Clearly, such a congested schedule would have a negative on Chelsea's trophy hopes, and probably would not do much for their Premier League aspirations either.
Yet even if they manage to get past Middlesbrough this week without the need for a second game, there is still the possibility for a fixture pile up later on.
With no midweek dates available for teams involved in European competition prior to the FA Cup semi-final weekend of April 13 and 14, the FA are investigating the potential for playing a quarter-final replay involving Manchester United or Chelsea - should one be required - on a weekend, only three of which are available.
In all probability, March 16 or 17 would be ruled out because of policing and ticketing issues, whilst March 31 follows immediately after the international break.
That would leave April 6, which for Chelsea would mean the postponement of a home game with Sunderland.
Of more significance, it would mean the Manchester derby, currently pencilled in for Old Trafford on Monday, April 8 but set to be moved to April 6 if United make it past Real Madrid to reach the Champions League quarter-finals, being re-arranged.
Although somewhat complicated, such a scenario might actually appeal to Sir Alex Ferguson as, if United are still in the Champions League, they would go into the Manchester City encounter at a significant disadvantage given Roberto Mancini has a completely free week to prepare for a game that, in all probability, his side have to win if they are to retain their title.
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