Goals from Matt Holland and Fabian Wilnis weren't enough to stop Town's Legends from falling to a 3-2 defeat to their Colchester counterparts at the Weston Homes Community Stadium this afternoon.
Tom English, Gary Bennett and Teddy Sheringham scored for the U's with Wilnis also hitting the post for the Blues.
Both sides fielded extensive squads of veterans augmented by fans who won auctions with the match raising funds for the clubs' academies.
The teams played for the Ross Crouch Memorial Trophy, which remembers the former Colchester youth player, whose father Nigel was with Town in the 1970s and whose uncle Steve Foley coached at Portman Road having previously held numerous roles at at Layer Road.