After seemingly failing to make the grade as a Gunner the club was looking to cash in on the Frenchman on that occasion; with the player himself increasingly tired of being used as a utility player rather than in his favoured central midfield role.
A deal was even reportedly agreed with Birmingham City however Flamini decided to stay and fight for his place in the first-team during the final year of his contract.
But the 2007-08 season was far more productive for the defensive midfielder; when he formed an excellent partnership with Cesc Fabregas in the heart of Arsenal’s defence.
He then signed a deal with AC Milan worth €5.6 million over the next four years.
So if those two summers were in direct contrast the French international may be pinching himself at the sheer familiarity this summer currently has with last.
As once again he does not know whether he will be an AC Milan player next season or not.
Last summer Milan were rightly cautious about offering him a new deal at the club. He had spent almost the entire 2011-12 season out after a career threatening knee injury and subsequent operation.
In the end they felt it was a risk they were not willing to take and released him when his contract expired that summer.
Then, in a dramatic U-turn, they agreed a new deal with the player who took a significant reduction in his wages and only asked for a one-year-deal in order to earn the renewal.
This summer that deal once again runs out and he finds himself on the cusp of becoming a free agent by this time next week.
Reports in Italy suggest that Milan and Flamini differ on the length of the deal; with the club willing to offer a two-year deal and Flamini after three.
That is despite him making just 21 appearances this campaign.
So once again Flamini will be a free agent once again this summer which will certainly alert the attention of potential Premier League suitors.
But don’t get too excited as if history is anything to go by Flamini will eventually agree a revised deal at the San Siro.
image: © Ronnie Macdonald