The 1990-91 season witnessed a significant improvement in Boro’s performances as they improved on the debacle of the previous campaign as they finished the season off in 7th place. They enjoyed a fine run in the Rumbelows Cup as they reached the forth round of the competition, losing 3-2 against Aston Villa.
The 1991-92 season saw Boro fair even better as they enjoyed a fantastic run in the league, finishing the season off in second position, gaining 80 points along the way to success. New players had come through the club, including, Curtis Fleming, Alan Moore and Robbie Mustoe. The season was capped off by fantastic cup runs, including a semi final finish in the league cup, narrowly losing out against eventual winners, Manchester United in the second round of the competition. They also had a fine run in the FA cup that saw the club reach the fifth round, suffering defeat against Portsmouth, losing a thrilling encounter 4-2.
Middlesbrough returned to the top flight for the 1992-93 season, however their stay was short lived as they finished the campaign off in 21st place, in turn relegating the club back to the second tier of English football. Boro could only manage a forth round finish in the FA Cup, losing against fellow relegation rivals, Nottingham Forest.
The 1993-94 season saw plenty of change go on at the club and they could only manage a 9th place finish, just missing out on a play off birth. Robbie Mustoe and Phil Stamp were in great form during the campaign. Boro were knocked out of the FA Cup in the third round, losing against Cardiff City 2-1 after extra time played.