The 1985 – 1986 season was the first year which saw Chris Nicholl in charge at the club as the Saints endured on a decent 14th position finish in the top flight by the end of the season. The pleasure from their season came from their fine run in the FA cup that saw the club reach the semi finals of the cup competition as they suffered a 3-0 defeat against Liverpool in a match played at White Hart lane. The Saints reached a semi final in a cup competition again the following season as they met Liverpool once again, this time in the league cup as they suffered a 3-0 defeat against the mighty Liverpool. For much of the late 1980’s the Saints hovered around the top end of the bottom half of the table, however they enjoyed a fine run during the 1989 – 1990 season as they finished the campaign off in an impressive seventh position finish. They also reached the quarter finals of the league cup, suffering a 2-0 defeat against Oldham Athletic in the last eight of the cup competition.
The 1989 – 1990 Southampton side included players like, Tim Flowers, Jason Dodd, Francis Benali, Jimmy Case, Neil Ruddock, Rodney Wallace, Glenn Cockerill, Paul Rideout, Barry Horne and Matthew Le Tissier.