Danny Wallace and John Burridge left during the campaign, while Ian Andrews, Sammy Lee and Oleksiy Cherednyk were brought in during the second half of the season.

Following several disappointing years, the Saints enjoyed good spells of form throughout 1989–90, including several high-scoring wins and victories over title contenders such as Liverpool, Aston Villa and Arsenal.

In the FA Cup, Southampton beat title contenders Tottenham Hotspur in the third round, followed by a narrow victory over Second Division side Oxford United.

[6] After Burridge's departure in October, Southampton brought in Celtic goalkeeper Ian Andrews on loan in December as backup for Tim Flowers, before signing him permanently for a fee of £200,000 in January 1990.

[9] In April, Blake – having returned from Colchester the previous month – was loaned out again, this time to Shrewsbury Town in the Third Division; come the end of the season, he would join the club permanently.

The first two, on the same day at the end of July, saw the Saints beating non-league opponents Bath City and Farnborough 3–1 and 6–0, respecitvely, with Matt Le Tissier scoring a hat-trick in the latter.

[1] A 0–3 thrashing at the hands of Everton was followed by a narrow 2–1 win over Aston Villa, after which the Saints shared eight goals with Norwich City at Carrow Road, in a match described by club historians as "remarkable".

[13] The first was an away victory over Queens Park Rangers, which saw the Hampshire side pick up two goals in the last three minutes after the London-based hosts threatened a late comeback.

[14] Despite these strong displays, it would be another month before the club won again, as they picked up two draws (against Tottenham Hotspur and Chelsea) and two marginal defeats (at Manchester United and Coventry City).

[14] Southampton's last game in November saw them score six goals in a league fixture for the first time since April 1984, as they beat Luton Town (who had thrashed the Saints 6–1 the previous season and 7–0 in 1985–86)[15] 6–3 at The Dell.

[14][16] December saw the club pick up narrow wins over strugglers Manchester City and defending champions Arsenal, while dropping points against Nottingham Forest and eventual relegatees Millwall and Sheffield Wednesday.

[24] Despite the tie taking place at White Hart Lane, the visiting Saints dominated most of the first half, breaking the deadlock just before the half-hour mark through Matt Le Tissier, who converted a setup from Jimmy Case.

[25] The fifth round of the tournament saw Southampton drawn away to Liverpool, the defending FA Cup champions and current First Division leaders, whose only loss of the season had come at the hands of the Saints.

[25] Playing without top scorer Le Tissier, the visitors struggled throughout the opening half of the game, eventually conceding five minutes before the break to Ian Rush.

[25] The second half saw the hosts continue to take advantage of their chances on goal, with a Peter Beardsley chip just after the hour mark doubling their lead, before Steve Nicol would complete the 3–0 win later on.

[26] In the third round, Southampton edged out First Division strugglers Charlton Athletic by a single goal, scored by Glenn Cockerill just after the half-time break.

[26] In the fourth round, a goalless draw at Second Division side Swindon Town made way for a replay at The Dell which the Saints won 4–2 after extra time, thanks to winning goals from Matt Le Tissier and Rod Wallace.