1998–99 FA Cup

First round

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.

Second round

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.

Third 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.

Fourth round

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.

Fifth round

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.

Sixth round proper

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.

Semi-finals

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, 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.

The replay was notable for a disallowed Arsenal goal, 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, intercepting a pass near the half way line, before taking the ball past five Arsenal defenders and scoring past goalkeeper David Seaman. 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.

Final

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.

Media coverage

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.