1. Luton 3-2 Arsenal, 1988
Even though they were in the same division as their opponents, Luton Town were given little chance on a sunny day at Wembley against the League Cup holders, whose manager George Graham was assembling the side that would win the league 13 months later. Town took an early lead through Brian Stein, but normal service was resumed when Arsenal powered past with two goals in three second-half minutes from Martin Hayes and Alan Smith – and then won an 80th-minute penalty.
Stand-in goalkeeper Andy Dibble turned Nigel Winterburn’s spot-kick around the post to give the Hatters hope – and then minutes later came the kind of comical defensive failure all but eradicated under Graham. Nervy stand-in centre-back Gus Caesar resembled Benny Hill on speed in a chicken pen as he hashed a clearance, allowing Stein to cross for Danny Wilson to head home. As Arsenal attempted to collect their thoughts for extra time, Stein scored a 90th-minute winner to give Luton their only major trophy.