Legendary Arsenal manager Arsene Wenger has admitted his mistake in letting Matthew Upson leave the club in 2003. Wenger has consistently revealed in the past that the decision was one of his worst as the Gunners boss. Matthew Upson became an Arsenal player in 1997 when the North Londoners paid £2m to sign him. Matthew Upson was signed from Luton Town shortly after he made his professional debut at the club.

Upson didn’t really settle at the club as he was farmed out on loan three times. The 41-year-old went to Nottingham Forest in 2000 and that loan spell ended with him making just one appearance for the club. Matthew Upson was then sent on loan to Crystal Palace in the following year. At the South London club, the centre back played seven times in the league before returning to Arsenal in the summer of 2001.

Matthew Upson embarked on a third successive loan spell from Arsenal when he joined Reading in 2002. He played 14 league matches during his time with the Royals. He spent the whole of the next season (2002/03 season) at Arsenal as the Gunners missed out on the Premier League title to rivals Manchester United. During his time as an Arsenal player, he failed to hit the back of the net in 35 appearances in the Premier League. Matthew Upson left Arsenal to join Birmingham City in January 2003 for an initial fee of £1m that eventually rose to £3m when the add-ons mere met. The 21-cap England international was a regular in the Birmingham City team as he scored five goals in 113 league games before leaving the club for West Ham United after Birmingham City suffered relegation in 2007. The Hammers paid £7.5m for him and the player went on to make 131 league outings for them, netting four goals in the process.