1998–99 FA Cup
| Country |
 England Wales
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|---|---|---|---|
| Teams | 558 | ||
| Champions | Manchester United (10th title) | ||
| Runners-up | Newcastle United | ||
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The 1998-1999 FA Cup was won by Manchester United, who beat Newcastle United 2–0 in the final at the old Wembley Stadium. The goals were scored by Teddy Sheringham after 11 minutes, less than two minutes after coming on as a substitute for Roy Keane, and Paul Scholes on 53 minutes. It was the second leg of an historic Treble for Manchester United; having already won the Premier League title the previous weekend, they went on to win the UEFA Champions League the following Wednesday.
The First Round featured those non-league teams who had come through the qualifying rounds and the teams from the third and fourth tiers of the English football league system. The matches were played on 14 November 1998. There were ten replays, with three ties requiring a penalty shootout to settle them.
The second round of the competition featured the winners of the first round ties. The matches were scheduled to be played on Saturday, 5 December 1998, with eight replays and two penalty shootouts required, each of which featured a team who won on penalties in the previous round.
The third round of the season's FA Cup was scheduled for Saturday, 2 January 1999. This round marked the point at which the teams in the two highest divisions in the English league system, the Premier League and the Football League First Division (now known as the Football League Championship). There were six replays, with none of these games requiring a penalty shootout.
The Fourth Round ties were played with the thirty-two winners of the previous round. The matches were originally scheduled for Saturday, 23 January 1999. There were three replays.
The Fifth Round matches were scheduled for Saturday, 13 February 1999. There were three replays, and one game re-played, Arsenal had beaten Sheffield United in the original tie. However, both sides felt that Arsenal's winning goal had been gained unfairly. Arsenal's boss Arsene Wenger wrote himself into FA Cup folklore with an act of sportsmanship that saw him offer to play the game again after Marc Overmars scored following Kanu's failure to return the ball to the Blades following an injury.
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