1988–89 Southampton F.C. season

Southampton made two main signings in the summer of 1988, bringing in Russell Osman to replace outgoing centre-back Kevin Bond, and re-signing former Saints youth player Paul Rideout to boost their forward line.

Towards the end of the season, manager Chris Nicholl brought in Barry Horne, Neil Ruddock, Micky Adams and Jason Dodd, while Colin Clarke left permanently for Queens Park Rangers after a loan spell at Bournemouth.

The league campaign was one of mixed fortunes for the Saints, who enjoyed strong spells of form during the early and latter stages of the season, but went through a period of 17 games without a win between November 1988 and March 1989 which saw them drop steadily down the table.

In the FA Cup, Southampton were knocked out in the third round by fellow First Division side Derby County, who beat the Saints 2–1 after extra time in a replay at The Dell days after a 1–1 draw at the Baseball Ground in the initial fixture.

[7] After a poor run of form leading up to the new year, Southampton attempted to sign Yugoslavian defender Miloš Drizić from FK Rad in January, but the application for his work permit was rejected by the Football Association.

[9] In March, out-of-favour striker Colin Clarke was sold to Queens Park Rangers after a short loan spell at Bournemouth, bringing in £800,000 to the club for further signings.

[19] The run included one draw and three wins: 2–1 over Tottenham Hotspur thanks to a Glenn Cockerill brace; 2–0 over strugglers Charlton Athletic; and 3–1 over recently promoted Aston Villa, with two goals for Matt Le Tissier.

[18] A dry spell throughout late November and December saw Southampton draw five of their next six fixtures, including games against Nottingham Forest and Newcastle United in which they dropped points from leading positions.

[20] The new year brought Southampton's worst run of form of the season, as they lost five league games in a row between 31 December and 4 February, dropping all the way down to 15th in the table.

[8] The Saints also lost 1–3 at home to Middlesbrough, who had only recently been promoted as Second Division play-off winners, and would ultimately be relegated back to the second flight at the end of the season.

[8] Southampton picked up points later in February with draws against Everton, Sheffield Wednesday and Charlton Athletic, but additional losses saw them drop as low as 18th – the first relegation place – after a total of 17 league games without a win up to the end of March.

[23] By the end of the run, Southampton had made it back up to 13th place in the First Division table, six points clear of the relegation zone, with ten wins, 15 draws and 13 defeats.

[28] In the second round, the Saints were beaten 2–1 by Crystal Palace, with Alex Dyer scoring the decisive goal in the final minutes to break a deadlock made by Rod Wallace in the second half.

In October, the Saints were hosted by Westbury United of the Western League to mark the opening of floodlights, with the top-flight visitors winning 12–1 thanks to goals from eight different players.

[14] The final two unofficial games of the season came in April and May, as the Saints beat the Royal Hussars armed forces side 15–1 (Rideout scored eight times in this match) and won 2–1 against German club Carl Zeiss Jena.

[29] Midfielder Jimmy Case and defender Russell Osman featured in 45 games each, while Matt Le Tissier finished as the season's second-highest scorer with 11 goals in all competitions.

After two seasons as the club's top scorer, Colin Clarke was sold to Queens Park Rangers for a record £800,000 partway through 1988–89.
After Clarke's sale, Micky Adams was signed from Leeds United for £250,000. He would go on to make over 150 appearances for the Saints during a five-year spell.
Matt Le Tissier was Southampton's second-highest scorer in the league during 1988–89 with nine goals.