The 1990 Football League Second Division play-off final was an association football match which was played on 28 May 1990 at Wembley Stadium, London, between Sunderland and Swindon Town. The match was to determine the third and final team to gain promotion from the Football League Second Division, the second tier of English football, to the First Division. The top two teams of the 1989–90 Football League Second Division season gained automatic promotion to the First Division, while the clubs placed from third to sixth place in the table took part in play-off semi-finals; Swindon Town ended the season in fourth position, two places ahead of Sunderland. The winners of these semi-finals competed for the final place for the 1990–91 season in the First Division. Newcastle United and Blackburn Rovers were the losing semi-finalists. This was the first season that the play-off final was determined over a single match and the first to be held at Wembley.

The match was refereed by John Martin and played in sunny conditions in front of a Wembley crowd of 72,873 spectators. Although Sunderland made a better start, Swindon dominated the fixture and after missing a number of chances, took the lead midway through the first half when Alan McLoughlin scored via a deflection from Gary Bennett. Swindon had several further chances to score but the second half was goalless and the match ended 1–0. Swindon Town were later demoted two divisions after being found guilty of financial irregularities which resulted in Sunderland gaining promotion. On appeal, Swindon's punishment was reduced to immediate relegation back to the Second Division.

Swindon ended their following season in 21st place in the Second Division, two points above the relegation zone. Sunderland were relegated back to the Second Division by the end of the next season, finishing in 19th place.

Swindon Town finished the regular 1990–91 season in fourth place in the Football League Second Division, the second tier of the English football league system, two places ahead of Sunderland on goal difference. Both therefore missed out on the two automatic places for promotion to the First Division and instead took part in the play-offs, along with Newcastle United and Blackburn Rovers, to determine the third promoted team. Swindon Town finished eleven points behind both Sheffield United (who were promoted in second place) and league winners Leeds United who had secured the title on goal difference.

Sunderland's opposition in their play-off semi-final were their Tyne–Wear derby rivals Newcastle United, with the first leg being played at Roker Park in Sunderland on 13 May 1990. The game proved to be ill-tempered with a total of seven players were booked, including a red card being shown by the referee: Sunderland's Paul Hardyman was dismissed after a foul on the Newcastle goalkeeper John Burridge who saved Hardyman's second half injury-time penalty. The match produced no shots on target and ended goalless. The second leg was played at St James' Park in Newcastle three days later. Eric Gates opened the scoring for the visitors when he converted a low cross from Gary Owers. Marco Gabbiadini then doubled Sunderland's lead in the 86th minute which led to a pitch invasion from the home supporters: the referee halted play and withdrew the players to their dressing rooms for twenty minutes while police restored calm. The final four minutes were played out without further addition to the score, and Sunderland qualified for the final, with a 2–0 aggregate victory.

Swindon Town faced Blackburn Rovers in the other play-off semi-final and the first leg was played at Ewood Park in Blackburn on 13 May 1990. The visitors took the lead after half an hour as Steve White from a David Kerslake break. Swindon dominated the match and Peter Foley doubled their lead in the 55th minute with a volley from at least 25 yards (23 m). Andy Kennedy scored a consolation goal in the 73rd minute as the match ended 2–1 to Swindon. The second leg of the semi-final took place at the County Ground three days later. A weak backpass from Blackburn defender David Mail allowed Duncan Shearer to intercept and score, making it 3–1 on aggregate to the home side. Minutes later, Shearer then went clear down the left wing and his pass was converted by White from close range. Midway through the second half, Howard Gayle's 30-yard (27 m) strike was deflected by Ross MacLaren past Fraser Digby in the Swindon goal to make it 2–1 on the day, but Swindon progressed to the final with a 4–2 aggregate win.

Neither side had featured in a play-off final although Swindon Town had lost in the semi-finals during the 1989 Football League play-offs. Swindon Town's last visit to Wembley Stadium was 21 years prior when they beat Arsenal 3–1 in the 1969 Football League Cup Final. This was Sunderland's fourth competitive trip to Wembley, the last time ending in a 1–0 defeat to Norwich City in the 1985 Football League Cup Final. They had also participated in the Football League Centenary Tournament, a friendly competition hosted at Wembley across two days in 1988, where they were knocked out in the first round on penalties by Wigan Athletic. They had last featured in the First Division in the 1984–85 season when they were relegated in 21st place. Swindon had never played at the top tier of English football but had been twice in four seasons, winning the Fourth Division in the 1985–86 season and the 1987 Football League Third Division play-off final. It was expected that around 40,000 Sunderland fans would make the tip to Wembley, and both clubs confirmed that they had sold their original allocation of 30,000 tickets. There was speculation in the media that the match would be a sell-out, with around 80,000 fans expected to attend. A Wembley official stated that both clubs had requested more than their official allocation of tickets and they were "staggered" by the interest in the match. This was the first play-off final to take place in a single match at Wembley Stadium: the previous three seasons had seen the play-off winners being determined after two legs, one match being played at the home ground of each finalist.

Sunderland were undefeated in the two games between the clubs during the regular league season: they won 2–0 at the County Ground in August 1989 before drawing the return fixture 2–2 at Roker Park in December that year. Sunderland's top scorer for the regular season was Marco Gabbiadini with 25 goals in all competitions (21 in the league and 4 in the League Cup), followed by Gordon Armstrong (13 goals; 8 in the league, 1 in the FA Cup, 3 in the League Cup and 1 in the Full Members' Cup). Leading Swindon's goal-scoring chart were Duncan Shearer with 26 (20 in the league, 1 in the FA Cup, 4 in the League Cup and 1 in the Full Members' Cup) and Steve White with 25 (18 in the league, 5 in the League Cup and 2 in the Full Members’ Cup).