Oldham 1990: 3-3, 2-1
Oldham 1994: 1-1, 4-1
Crystal Palace 1995: 2-2, 2-0
Chelsea 1996: 2-1
Arsenal 1999: 0-0, 2-1
Arsenal 2004: 1-0
Newcastle 2005: 4-1
Watford 2007: 4-1
Everton 2009: 0-0, on 2-4 pens
Click on the image for pictures from each year.
In the first eight, he took the side through to the final. The only defeat, to Everton two years ago, came in a penalty shoot-out after a fixture pile-up convinced the boss to shuffle his pack.
Ahead of Saturday's eagerly-awaited clash with Manchester City, we take a look at the last-four encounters that have helped the Reds become the competition's most successful side.
Oldham 1990 (Maine Road)
Broadcast live to millions around the world, United and the Latics thrilled the masses with a 3-3 draw at Maine Road. Joe Royle's battlers refused to yield and took the game to a replay, where Mark Robins rolled in the winner to set up a Wembley final against Crystal Palace.
Oldham 1994 (Wembley, Maine Road)
The Latics again stood in United's way and the season was in danger of collapsing until