3. Man United 0-3 York City – 2nd Round 1995
Another massive upset, as third-tier side York managed to beat the eventual Premier League and FA Cup winners at Old Trafford. York had started badly in the season and for many the tie was viewed as an easy victory for the Red Devils. The Minstermen though had other ideas. They took the game to United and created some great opportunities, especially in the second half, and eventually bagged three goals through Barnes (twice) and Barras, despite the home side having a team that consisted of Phil Neville, David Beckham and Ryan Giggs.