The Frenchman was a graduate of the Arsenal academy, and made his debut when he replaced Gunners legend Thierry Henry during a 4-1 win over Fulham in the 2001/02 season.
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He spent another five seasons at Arsenal, but found first team oppourtunities hard to come by, only making a further 28 league appearances for the Gunners during that time.
"I left for Middlesbrough because I forced the move, because I was 24 and needed to play," Aliadiere admitted to French outlet SFR Sport.
The striker was sent out on loan on three occasions during his time at Highbury - to Celtic, West Ham and Wolves. But has admitted that his former manager did want him to stay at the club.
"He [Arsene Wenger] was telling me to stay because I'd play. Now, I regret it.
"For me, Arsenal was the ideal club, and I wanted to do my whole career and spend my life there
"It felt like a failure when I felt I had to leave, but it's true that now, I arrived at the same time at Thierry Henry and left at the same time at Thierry Henry.
"If I'd stayed an extra year, maybe I could have taken his spot."
Aliadiere went onto score 12 goals in 86 appearances for Middlesbrough before being released in July 2010.
He is now 35-years-old and currently a free agent after leaving French Ligue 2 club FC Lorient at the end of last season.