The 1938–39 FA Cup was the 64th season of the world's oldest football cup competition, the Football Association Challenge Cup, commonly known as the FA Cup. Portsmouth won the competition for the first time, beating Wolverhampton Wanderers 4–1 in the final at Wembley. As this was the last full FA Cup competition before the Second World War, Portsmouth held the trophy until the end of the 1945–46 season.

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.

Most participating clubs that were not members of the Football League competed in the qualifying rounds to secure one of 25 places available in the first round.

The 25 winners from the fourth qualifying round were North Shields, Horden Colliery Welfare, Lancaster City, Stalybridge Celtic, Chorley, Workington, Runcorn, Scunthorpe & Lindsey United, Gainsborough Trinity, Wellington Town, Kidderminster Harriers, Peterborough United, Colchester United, Lowestoft Town, Chelmsford City, Apsley (later to be known as Hemel Hempstead Town), Hayes, Corinthian, Folkestone, Guildford City, Walthamstow Avenue, Tunbridge Wells Rangers, Street, Cheltenham Town and Yeovil & Petter's United.

Advancing to the competition proper for the first time were Runcorn, Colchester United, Apsley and Street, while Lowestoft Town was doing so for the first time since 1926–27, Horden Colliery Welfare for the first time since 1925-26, and Chorley for the first time since 1899-1900.

Hayes was the only club to progress from the extra preliminary round to the first round proper, defeating Wycombe Wanderers, Yiewsley, Chesham United, Banbury Spencer, Southall and Newport (IOW) to secure their place in the main draw. However, Chelmsford City was the most successful non-league club this season, moving from the preliminary round to the fourth round proper and defeating Barking, Ford Sports (Dagenham), Crittall Athletic, Romford, Dulwich Hamlet, Kidderminster Harriers and Football League sides Darlington and Southampton in their history-making run.

At this stage, 41 clubs from the Football League Third Division North and South joined the 25 non-league clubs that came through the qualifying rounds. Barnsley, York City and Notts County were given byes to the third round. To make the number of matches up, non-league Scarborough and Bromley were given byes to this round, with Bromley having won the previous season's FA Amateur Cup.

34 matches were scheduled to be played on Saturday, 26 November 1938. Eight were drawn and went to replays in the following midweek fixture.

The matches were played on Saturday, 10 December 1938. Four matches were drawn, with replays taking place in the following midweek fixture. One of these, Halifax Town vs. Mansfield Town, then went to two more replays before being settled.

The 44 First and Second Division clubs entered the competition at this stage along with Barnsley, York City and Notts County.

The matches were scheduled for Saturday, 7 January 1939, although seven matches began at later dates. Eight matches were drawn and went to replays, with one of these requiring a second replay to settle the fixture.

The matches were scheduled for Saturday, 21 January 1939. Five games were drawn and went to replays, of which two went to a second replay. Chelmsford City was the last non-league club remaining in the competition, participating in their ninth round of this tournament.

The matches were scheduled for Saturday, 11 February 1939. There were four replays, of which two went to second replays.

The four sixth round ties were scheduled to be played on Saturday, 4 March 1939. There was one replay, in the Huddersfield Town–Blackburn Rovers match.

The semi-final matches were played on Saturday, 25 March 1939. Wolverhampton Wanderers and Portsmouth won their matches to meet in the final at Wembley.

The 1939 FA Cup Final was contested by Portsmouth and Wolverhampton Wanderers at Wembley. Portsmouth won 4–1, with goals from Bert Barlow, John Anderson and two by Cliff Parker. Dicky Dorsett scored Wolves' effort.

As a result of the suspension of the FA Cup for the duration of the Second World War, the next FA Cup final was not until seven years later in 1946, thereby enabling Portsmouth fans to claim that their team has held the Cup for the longest time.

29 April 1939
15:00 GMT

Portsmouth	4–1	Wolverhampton Wanderers
Barlow 29' Anderson 43' Parker 46', 71'		Dorsett 54'

Empire Stadium, Wembley, London

Attendance: 99,370

Referee: T. Thompson (Lemington, Newcastle upon Tyne)

Portsmouth

Wolves

• FA Cup Final Results 1872-

General

• Official site; fixtures and results service at TheFA.com
• 1938-39 FA Cup at rsssf.com
• 1938-39 FA Cup at soccerbase.com

Specific