
**2 May: Potential Europa League match versus Benfica or Eintracht Frankfurt
Assuming Chelsea does not get upset by Prague (like Sevilla did), they will face either Benfica or Frankfurt right after the United match. If Chelsea is this close to the final they should go all out regardless of opponent, but Chelsea should very much hope Benfica makes it through. The Portuguese side will not be easy, but Frankfurt would be a style clash that Chelsea just fell to with Wolves and Everton. The key difference would be that Frankfurt has one of Europe’s deadliest strike duos up top.
4 May: Watford at Home
If top four is still a realistic hope then Watford sandwiched by Europa League will be an incredibly tricky match. Watford is not unbeatable by any means (especially by the top six) but they remain dangerous and their place in the table is well earned. If a top four race is on, Chelsea will need all hands on deck. If top four is a lost cause, then this is a match where the Blues should rotate heavy as they focus on Europa League (assuming that they are still in the competition).
**9 May: Potential Europa League match versus Benfica or Eintracht Frankfurt
This is the hardest match of all to determine because it will be unclear how top four is looking or how Chelsea is looking on aggregate and with away goals. Again, Benfica would be a much better opponent for Chelsea than Frankfurt but regardless, if this match is happening Chelsea needs to go all out and ensure they make another final.
12 May: Leicester Away
Championship Sunday sees Chelsea face off against Brendan Rodger’s “new look” Leicester. If top four is still a potential result then Chelsea will need to keep an eye on Manchester United hosting (a probably relegated) Cardiff, Tottenham hosting Everton, and Arsenal away to Burnley (who could have their Premier League survival on the line). End the Premier League season with a bang no matter what, because there is a layoff after words regardless of whether it is the last match of the season or not.
**29 May: Potential Europa League final versus Arsenal, Napoli, Valencia, or Villarreal
Chelsea will have two weeks (and a trip to Boston) to think about the Europa League final. Hopefully, the Blues will be thinking of preparing for it rather than thinking about how nice it would be to be in it. Who the potential opponent is matters little. Arsenal, Valencia, and Villarreal could all need a win to get Champions League. Carlo Ancelotti would want a win with Napoli to show that the Italian side is well and truly his now.
Chelsea has a ways to go this season but there is also not much left to go at the same time. The final stretch can signal many things for Chelsea and has many exit ramps for various targets. What matters most is that the Blues look like they have a plan as the season beings the final stretch.