Mathieu Flamini yesterday dealt a significant blow to Arsène Wenger’s future plans by signing a four-year contract with AC Milan, as The Times reported he would last month, and the France midfield player is unlikely to be the only unwanted departure from Arsenal this summer.

Alexander Hleb, the Belarus midfield player, has confided in several of his team-mates that he is planning to join Inter Milan and his representatives are understood to have agreed a four-year deal with the Italian champions. With two years remaining on his contract, Arsenal will battle to keep hold of Hleb, with Wenger threatening to report Inter to Fifa allegedly for making an illegal approach that has yet to be made into a firm bid.

Hleb, 27, is understood to be frustrated by Arsenal’s failure to win silverware, as well as concerned that the club’s pay structure will prevent him earning what he could pick up elsewhere, particularly given the policy of awarding only one-year extensions to players approaching 30.

Arsenal’s pay policy has effectively cost them Flamini, who rejected two contract offers to sign a £50,000-a-week deal at Milan. The 24-year-old flew to Italy after attending Arsenal’s 1-0 win over Everton on Sunday, dining at the Giannino restaurant owned by Kaká, the Milan and Brazil forward, with club officials before having a three-hour medical at the club’s training ground yesterday.

Arsenal’s failure to keep Flamini will raise serious questions about their ability to compete with Europe’s leading clubs, but the departure of Jens Lehmann is less significant. The Germany goalkeeper yesterday thanked Wenger for permitting him a tearful farewell to the fans for the final 20 minutes against Everton, ensuring a turbulent final season at the club ended on good terms.

“It was quite emotional and I had one or two tears in my eyes, as it was a great farewell for me,” Lehmann said. “This farewell will always stay in my heart. In terms of life, in terms of learning something about football, in terms of being part of a team which is playing probably the most attractive football, Arsenal has been really good.”