Arsenal do not seem to be learning their lesson, with Bacary Sagna reportedly the latest player on the verge of walking out after being disillusioned by a new contract offer.
The future of Theo Walcott is already very much in the air, with the forward still not agreeing on a new contract with the Gunners. He will be free to talk to clubs outside England in January, while also having the option of leaving on a free when his contract ends at the end of the season.
Sagna's situation is not as dire, as his current deal ends in 2014, but the French international is reportedly upset with the Gunners board for only offering him a one-year contract extension.
The 29-year-old, who will hit 30 in February, is also not happy about Arsenal not offering a pay rise to the current £60,000 a week ($96,500) that he earns.
Walcott is still to agree on a new contract, although it is understood there has been some decent progress with Arsenal ready to increase their take-it-or-leave-it five-year offer of £75,000 a week ($120,000).
However, despite reports of some of Arsenal's most consistent players leaving, there is certain deadwood that needs to be taken out as soon as possible.
The likes of Marouane Chamakh, Andrey Arshavin and Johan Djourou are some of the highest earners at the club, despite being way down the pecking order, and Arsene Wenger is desperate to find new clubs for some of his players as he looks to bring in new faces in January.
One of those could be Fernando Llorente, after the Spanish international striker admitted he would definitely leave Athletic Bilbao when his contract expires in June, although he did insist he will look to remain with the club until the end of the season and not seek a move in January.
"It is not a financial issue because the offer (from Athletic) was unrefusable, but what happened in the media did not help," he said.
"That is one of the reasons. A bad atmosphere was generated with me on the field and that, along with many other things, made me decide not to renew my contract. Most of what has been published about my meetings with other clubs has been lies and has helped turn people against me. But I feel loved by the majority of the fans.
"There is clearly a section which does not like me, but I respect that. Some people want me to go. The new contract negotiations were very long and from the first moment I did not want to leave, but neither is it something I would blame on Athletic.
"What happened at the first European game of the season at San Mames left me very unhappy and I took the decision to leave.
"I am leaving on June 30. You also like to try other things too. I have been European and World Champion (with Spain). I have played for years at a good level."
A January move cannot be ruled out with Llorente's transfer fee set to be reduced considerably, seeing as he is on the last six months of his contract.
Arsenal have also been linked with moves for Adrian Lopez and Klaas-Jan Huntelaar, while there have been unconfirmed reports of a move for the prolific Napoli striker Edinson Cavani, although with the Dutchman's signing looks the most likely.
So will Arsenal regret another mass exit from their senior players in the summer, or can they agree to a new deal; and who will Wenger buy in January? Only time will tell.