The 1998–99 FA Cup (known as The AXA sponsored FA Cup for sponsorship reasons) was the 118th staging of the FA Cup. It 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 a historic Treble for Manchester United; having already won the Premier League title the previous weekend, they went on to win the 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.

The four quarter-final games were scheduled for Saturday, 6 March 1999, although only the Arsenal–Derby County game was played on this date. One of the ties, Manchester United–Chelsea, resulted in a draw which went to a replay, which United won.

Barnsley, who lost 1-0 at home to Tottenham Hotspur, were the last remaining non-Premiership team in the competition.

The semi-finals were played on Sunday, 11 April 1999. The Manchester United–Arsenal match went to a replay, which was won in extra-time by Manchester United.

The semi-final round was notable for the climax to the season-long rivalry between Arsenal and Manchester United. As the first game went to a nil-nil draw, although Roy Keane scored an offside goal for Manchester United, which in today's modern rules would have stood, the match went to a replay. This was to be the last replay of a drawn semi-final, as a rule change now allows for extra time and penalties to decide a tie at the first attempt.^[1]

The replay was notable for: a thirty-yard strike from David Beckham to open the scoring, a (correctly) disallowed goal scored by Arsenal, the sending-off of Roy Keane for a second bookable offence, a last-minute penalty save by Peter Schmeichel, and finally- and most memorably- a winning goal by Ryan Giggs. Giggs intercepted a wayward Patrick Viera pass near the half-way line, before taking the ball past five Arsenal defenders and beating Arsenal goalkeeper David Seaman with a fearsome left-footed strike into the roof of the net. It was hailed almost immediately as one of the greatest goals ever scored in the history of the competition.

Newcastle beat Tottenham in the other semi-final, ending the latter's hopes of an FA Cup/League Cup double.

The Final took place on 22 May 1999 and was played at the old Wembley Stadium, between Manchester United and Newcastle United. Manchester United had finished as champions and Newcastle 13th in the Premier League that season. The final was a slightly one-sided affair, Manchester United claiming a record 10th success with a 2–0 win. Goals from Teddy Sheringham and Paul Scholes were scored in the 11th and 53rd minutes respectively. It was the buildup to Manchester United's Treble. Manchester United also became the first team to win the double three times.

In the United Kingdom, ITV were the free to air broadcasters for the second consecutive season while Sky Sports were the subscription broadcasters for the eleventh consecutive season.