The Saints had a disappointing first campaign with Nicholl, finishing 14th in the First Division table – their joint lowest position since their 1979 promotion to the top flight.

Southampton's squad at the start of the 1985–86 campaign remained much the same as the previous season, with full-back Mick Mills the only major departure in the summer.

The first three were as part of a short West Indies tour, during which they beat domestic league rivals Manchester United 1–0, the Trinidad and Tobago under-21 team 7–3, and local side Trintoc 4–0.

[13] Southampton started their first season under Chris Nicholl poorly, picking up just four points from their first six games and immediately dropping down the table close to the relegation zone.

[16] A subsequent 0–1 loss at title challengers Liverpool had left the club 17th in the table,[17] after which Nicholl brought in midfielder Glenn Cockerill and defender Jon Gittens to bolster the struggling squad.

[18] At the beginning of December, Gerry Forrest was signed and the Saints beat Arsenal 3–0 at home, with goals coming from Kevin Bond, Armstrong and Moran.

[20] Several marginal 0–1 defeats in the final stages of the season – including against Chelsea, West Bromwich Albion and West Ham United – saw Southampton unable to make it above 14th in the league again, with their position confirmed by defeats against title chasers Everton (1–6) and mid-table side Tottenham Hotspur (3–5) in the final two games of the campaign (during which Keith Granger and Mark Blake made their first team debuts).

[22] Don O'Riordan equalised for the hosts, before Wallace doubled his tally and put the Saints back ahead on 40 minutes from a Glenn Cockerill assist.

[22] The visitors continued to apply most of the pressure after the break, with Wallace finally completing a hat-trick and securing his team's first away win in 10 months after 89 minutes.

[23] Another home tie followed in the fifth round, this time against Second Division opponents Millwall, past whom the Saints had edged on penalties after two goalless legs in the League Cup just a few months earlier.

[23] In their fourth FA Cup quarter-final in ten years, Southampton travelled to face another Second Division side, Brighton & Hove Albion, just five days after the victory over Millwall.

[24] Southampton were drawn in their second FA Cup semi-final in three years against defending First Division champions Liverpool, in a tie played at Tottenham Hotspur's stadium White Hart Lane.

[24] Shortly before half-time, centre-back Mark Wright broke his leg, which prevented him from finishing the season or playing in the upcoming 1986 World Cup.

The first leg, at The Den, ended in a 0–0 draw thanks to a "stunning" performance by Saints goalkeeper Peter Shilton, who saved a second-half penalty to keep his clean sheet.

[25] In the third round, Southampton played Birmingham City at St Andrew's, holding the hosts to a 1–1 draw to force a replay at home.

[25] Southampton's fourth round tie against Arsenal also ended in a draw necessitating a replay at home, which the visiting Gunners won 3–1 thanks to goals from Martin Hayes, Charlie Nicholas and Stewart Robson.

Attacking midfielder David Armstrong featured in the most fixtures of any player, as well as finishing as the season's top goalscorer – he scored 16 goals in 57 appearances across all three competitions, missing only one game in the league.