The 1985-86 campaign was not the greatest campaign for Spurs, they finished in a respectable 10th position in the league and were knocked out in the fifth and forth rounds of the FA Cup and league cup respectively. The 1986-87 season saw a huge improvement in Spurs league and cup form. For much of the campaign, Tottenham were firmly in the title race and they ended the season finishing third with 71 points, largely helped by the brilliance of Chris Waddle and Glenn Hoddle. Spurs were outstanding in the domestic cup competitions; they were eventually knocked out of the league cup in the semi finals against Arsenal, after forcing a replay. They had a marvellous run in the FA Cup which saw them through to the final. Clive Allen was inspirational up front for Spurs through out the tournament, and they lost 3-2 to Coventry City in the final, a disappointing end to a fantastic season.
After the success of the 86-87 campaign, Spurs completely faltered the following season, they crashed in the league as they managed to finish only 13th, their domestic cup performances were poor. They were knocked out early in the league cup as they lost 2-1 to Aston Villa, worse was to follow as Spurs embarrassingly lost 2-1 to Port Vale in the FA Cup forth round.
Spurs bought Paul Gascoigne from Newcastle for the start of the 1988-89 season and the deal paid off eventually. Spurs saw a significant improvement in league form as they finished the season off strongly in sixth position under their new coach, Terry Venables. They faired worse in cup competitions as they crashed out in the third round of the FA Cup against third division outfit, Bradford City.
Venbales bought England striker Gary Lineker to White Hart Lane in time for the 1989-90 season and he provided goals. His 24 goals helped Spurs finish in a highly impressive third position in the league. Their league cup form was also impressive; they reached the last eight, only being knocked out 3-2 against eventual winners, Brian Cloughs Nottingham Forest.