Not only did they have to put up with Cesc Fabregas being passed over by manager Arsene Wenger and making the switch to Chelsea, they have also seen the likes of Robin van Persie defect to Manchester United and a fair few of their players leave for other sides including Manchester City to boot.
Oh, and manager Arsene Wenger usually compounds the misery with his own performance in the transfer window, which is usually lacking at best.
This January however it could well be time for payback, with the Gunners linked to a move for long serving Chelsea goalkeeper Petr Cech who is reportedly available for around £7 million and would ideally like to remain in London, where he has been for the last decade and has a settled family.
Wanting to leave Chelsea is fair enough you might think, especially given Cech has done nothing to warrant being dropped bar be unfortunate to be at the club when Thibaut Courtois finally came back from his loan spells, but to go to Arsenal?
That is something Jose Mourinho would be rather reluctant to sanction one would imagine, with Cech a world class keeper who could make a difference to just about any side he decided to join – and Arsenal could quite easily be a title rival in the seasons to come, especially should they see manager Arsene Wenger finally depart or move upstairs.
Do Chelsea really want to see their Champions League final hero help them do that? Probably not given how hard it was for them to watch Frank Lampard don a Manchester City shirt.
Selling to a rival side in terms of domestic football is never ideal and whilst the term ‘rival’ is obviously rather loosely used for the minute to talk about Chelsea and Arsenal, they have been direct rivals for the title in the past and could well be again.
Selling to a side in Europe such as AC Milan would be the far better option for the fans and whilst not ideal for Chelsea to see Cech leave, it seems to be inevitable – but the Blues should take heed of that Lampard goal earlier this season and remember what former players can do to a club.
He might have to let Cech leave, but would Mourinho really send him across London to the Specialist in Failure? No way, Jose!
Chelsea fans. How would you feel if Arsenal really did sign Cech in January? Let us know your thoughts below or tweet us @LaFootyettes.