Like the previous season, Southampton did not make any signings in the transfer window ahead of the 1990–91 campaign, although Graham Baker, Mark Blake and Gerry Forrest all left the club.

Partway through the season, however, Nicholl did bolster the squad with the additions of Sergey Gotsmanov, Alan McLoughlin, Richard Hall, and the returning Jon Gittens.

Having led Southampton to their highest league finish since his arrival as manager, Chris Nicholl opted not to make any new signings during the summer 1990 transfer window.

[6] He was followed in December by another attacking midfielder, Republic of Ireland international Alan McLoughlin, who joined from Swindon Town in the Second Division for a Saints record fee of £1 million.

[7] The additions continued into the second half of the season – in February, promising young centre-back Richard Hall was signed from Fourth Division side Scunthorpe United for £200,000;[8] in March, Jon Gittens returned from Swindon Town – to whom the Saints had sold the defender just under four years earlier – for a fee of £400,000;[9] and the same month, Welsh midfielder David Hughes arrived from non-league side Weymouth as a trainee (he would turn professional at the beginning of the next season).

[15] Southampton started the 1990–91 league campaign slowly, picking up one draw (at last season's runners-up Aston Villa), one win (a narrow 1–0 victory over Norwich City) and two losses (against Luton Town and Nottingham Forest) in their first four fixtures.

This was followed by a 2–1 win over Coventry City and a 0–1 defeat at home to Derby County, who had only avoided relegation the season before by three points, after which Nicholl claimed that no one besides goalkeeper Tim Flowers "justified their place [in the team] or their wage packet".

[17] After a 1–1 draw at Wimbledon and a "comfortable" 3–1 win over Queens Park Rangers, the Saints lost four games in a row and dropped as low as 17th in the league table.

[20] 1991 started with a defeat at Sunderland, which was followed by a hard-fought 4–3 win away at Luton Town, in which top scorers Le Tissier and Rod Wallace shared the goals equally.

After a 1–1 draw at Highfield Road, the Saints progressed with a 2–0 replay win at home, with goals from Jimmy Case and Rod Wallace either side of half time giving them the victory.

The Saints went one up after just two minutes, when Neil Ruddock headed in a corner from Le Tissier, and continued to dominate the half when Glenn Cockerill came close twice and a Paul Rideout goal was disallowed due to offside.

[26] The home side continued to enjoy chances in the second half, with Cockerill coming close again, before Forest equalised in the 80th minute through Steve Hodge, forcing a replay.

[26] In the rematch at City Ground, Southampton came close to opening the scoring in the first few minutes, as Wallace hit the post and Ruddock saw his header cleared off the line by the Forest defence.

[26] Wallace did open the scoring in the 14th minute, but at half-time the teams were level after Nigel Jemson converted a penalty awarded for a "dubious" handball decision against Francis Benali.

The visiting Saints thrashed the hosts 5–0 in the first leg, with Alan Shearer scoring twice before Barry Horne, Rod Wallace and Neil Ruddock all added to the tally in the last ten minutes of the match.

[27] Southampton beat Ipswich Town and Crystal Palace 2–0 in the third and fourth rounds, respectively, with leading scorers Matt Le Tissier, Rod Wallace and Shearer sharing the goals.

In April, they beat Wessex League side Christchurch 5–0, with a hat-trick for Alan Shearer alongside goals for Matt Le Tissier and Rod Wallace.