The 1958–59 FA Cup was the 78th staging of the world's oldest footballcup competition, the Football Association Challenge Cup, commonly known as the FA Cup. Nottingham Forest won the competition for the second and, as of 2020, final time, beating Luton Town 2–1 in the final at Wembley. This is Luton Town's only appearance in an FA Cup final as of 2020. Matches were scheduled to be played at the stadium of the team named first on the date specified for each round, which was always a Saturday. Some matches, however, might be rescheduled for other days if there were clashes with games for other competitions or the weather was inclement. If scores were level after 90 minutes had been played, a replay would take place at the stadium of the second-named team later the same week. If the replayed match was drawn further replays would be held until a winner was determined. If scores were level after 90 minutes had been played in a replay, a 30-minute period of extra time would be played. The competition saw the remarkable progress of Norwich City, then a Division Three team, to the semi-finals, defeating Manchester United and Tottenham Hotspuralong the way, before losing in a replay to Luton Town. The "59 Cup Run" takes a notable place in Norwich's club history.
At this stage clubs from the Football League Third and Fourth divisions joined those non-league clubs having come through the qualifying rounds. Matches were scheduled to be played on Saturday, 15 November 1958, although the Bury–York City match was postponed. Ten were drawn and went to replays, with one of those going to a second replay.
The matches were scheduled for Saturday, 6 December 1958. Six matches were drawn, with replays taking place later the same week. One match went to a second replay.
The 44 First and Second Division clubs entered the competition at this stage. The matches were scheduled for Saturday, 10 January 1959, although six matches were postponed until later dates. Six matches were drawn and went to replays.
The matches were scheduled for Saturday, 24 January 1959, with three matches taking place on later dates. Six matches were drawn and went to replays, which were all played in the following midweek match.
Tie no
Home team
Score
Away team
Date
1
Bristol City
1–1
Blackpool
24 January 1959
Replay
Blackpool
1–0
Bristol City
28 January 1959
2
Preston North End
3–2
Bradford City
24 January 1959
3
Leicester City
1–1
Luton Town
24 January 1959
Replay
Luton Town
4–1
Leicester City
28 January 1959
4
Nottingham Forest
4–1
Grimsby Town
28 January 1959
5
Blackburn Rovers
1–2
Burnley
28 January 1959
6
Wolverhampton Wanderers
1–2
Bolton Wanderers
24 January 1959
7
West Bromwich Albion
2–0
Brentford
24 January 1959
8
Tottenham Hotspur
4–1
Newport County
24 January 1959
9
Accrington Stanley
0–0
Portsmouth
24 January 1959
Replay
Portsmouth
4–1
Accrington Stanley
28 January 1959
10
Norwich City
3–2
Cardiff City
24 January 1959
11
Chelsea
1–2
Aston Villa
24 January 1959
12
Worcester City
0–2
Sheffield United
24 January 1959
13
Charlton Athletic
2–2
Everton
24 January 1959
Replay
Everton
4–1
Charlton Athletic
28 January 1959
14
Stoke City
0–1
Ipswich Town
24 January 1959
15
Colchester United
2–2
Arsenal
24 January 1959
Replay
Arsenal
4–0
Colchester United
28 January 1959
16
Birmingham City
1–1
Fulham
28 January 1959
Replay
Fulham
2–3
Birmingham City
4 February 1959
Fifth round proper
The matches were scheduled for Saturday, 14 February 1959. Four matches went to replays in the following midweek fixture, with two of these requiring a second replay to settle the tie.
The four quarter-final ties were scheduled to be played on Saturday, 28 February 1959. Three of the four games went to replays.
Tie no
Home team
Score
Away team
Date
1
Blackpool
1–1
Luton Town
28 February 1959
Replay
Luton Town
1–0
Blackpool
4 March 1959
2
Nottingham Forest
2–1
Bolton Wanderers
28 February 1959
3
Aston Villa
0–0
Burnley
28 February 1959
Replay
Burnley
0–2
Aston Villa
3 March 1959
4
Sheffield United
1–1
Norwich City
28 February 1959
Replay
Norwich City
3–2
Sheffield United
4 March 1959
Semi finals
The semi-final matches were played on Saturday, 14 March 1959. Nottingham Forest and Luton Town won their matches to meet in the final at Wembley. ---- ;Replay