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Tommy started his career with Southampton in 1990. He was loaned out to Wigan Athletic in 1991 and never really pushed for a first team place until 1993.Widdo played Premiership football for The Saints until 1996 and transfered to The Mariners for £300,000 at the start of the 1996/1997 season after making around 80 apperances at The Dell.
Widdrington did well for Town despite a lot of injury trouble, he scored a fantastic goal against Southend United on the last day of the 96/97 season striking it from 35 yards out.
Widdrington played his last game for Grimsby towards the end of the 1998/1999 season when he was loaned out to Port Vale for the final 3 months of the season.
At the end of the season Port Vale signed out of contract,transfer listed Widdrington on a free transfer. Tommy played probably the best football of his career at Port Vale and made just over 80 apperances for Vale before being released at the end of the 2000/2001 season.
Tommy moved north and joined up with Hartlepool United, he was a regular for the club and earned promotion to Division 2 with the club in his last year the 2002/2003 season.
Widdo made his next port of call at Macclesfield Town after being released by Hartlepool. Tommy settled in quickly and became an indespensible player for the Division 3 strugglers.
In January 2005, Tommy decided to call it a day at Macclesfield and in a twist , joined former club Port Vale on a non-contract basis, Widdo remains at Vale Park, but for how long.