Having recently been eliminated from the EFL Cup and gotten off to a stuttering start in the Premier League, Frank Lampard will be hoping for a strong showing in Europe this season.
Last campaign, the Blues bowed out in the round of 16 to eventual winners Bayern Munich. This tough draw could have been averted if they'd managed to top a straight forward Group H, but instead they finished behind Valencia on head-to-head record.
The Blues will be aiming to avoid a repeat of this and all eyes will be firmly fix on Thursday's draw. With Chelsea in Pot Two, which teams will Lampard be hoping join them in their group? 90min went through all the eventualities to find out.
Best Possible Draw
Zenit Saint Petersburg, Chelsea, Olympiakos, FK Krasnodar
No disrespect meant to Zenit Saint Petersburg but they are by far the weakest team in Pot A.
If the Blues did draw them, they would be dealing with a frontline of Sardar Azmoun and Artem Dzyuba. That's a far less daunting prospect than the likes of Karim Benzema, Neymar and Cristiano Ronaldo.
Drawing the Russian champions would also see former Blues wideman Yuri Zhirkov face off against his old club - which we be good fun. Almost as much fun as seeing how Dejan Lovren fares against the Blues' wealth of attacking talent.
As for the rest of Chelsea's 'best case scenario' group, Olympiacos in Pot Three would be a great draw. The Greek side have not progressed from their Champions League group since 2011 and have experienced some gubbings at the hands of English sides in recent times.
In terms of Pot Four, no one particularly dangerous stand out - and that's taking into account every possible result from the remaining playoff games.
Red Bull Salzburg would be a nice draw. Although one of the eastern European minnows may seem appealing, this will add unnecessary air miles onto Chelsea's season. Better keep in safe and hope for a short trip to Austria instead.
Worst Possible Draw
Bayern Munich, Chelsea, Inter, Stade Rennais
Chelsea will have only just gotten over the 7-1 thrashing Bayern subjected them to over two legs last season. The last thing they will want is to have to face Die Roten again this year.
Hansi Flick's team are one of the most devastatingly incarnations of Bayern of all time, possesses barely any chinks in their armour. The Blues shaky defence will particularly want to avoid facing off against the likes of Robert Lewandowski, Serge Gnabry and Leroy Sane.
Another poor draw for Chelsea would be Inter. The Nerazzurri are coached by former Blues boss Antonio Conte and are seriously contenders for the Serie A title this season. Buoyed by a string of summer recruits, Conte will be especially motivated to get one over his former employers.
In Pot Four, Lampard will be dreading a potential trip to face Stade Rennais, who currently sit atop the Ligue 1 table, and four points clear of PSG.