The 1998-99 season was a fine one for Boro and manager Bryan Robson; Middlesbrough enjoyed a fantastic return to the premiership, finishing their season off in ninth place. They faced tough opposition in the domestic cup competitions, meeting ‘treble’ winners, Manchester United in the third round of the FA cup, losing the match 3-1. Gary Pallister moved back to Middlesbrough to start a second spell at the club. Mark Schwarzer was also in fine form in goal for Boro as they enjoyed their season back in the top flight.
The 1999-2000 campaign was a very respectable one for Boro, although they failed to do as well as the previous campaign. A mid table finish of 12th place was by no means a disaster. They most notably reached the quarter finals of the league cup, however they could not overcome the obstacle of beating lower division opponents, Tranmere Rovers in the last eight, a side that went on to reach the final. The French football international, Christian Karembeu, proved to be a revelation at Boro despite only playing for the club for a single season.
Middlesbrough saw a decline in their league performances during the 2000-01 season and they finished it off in 14th place. The club also endured miserable domestic cup performances as they lost to Wimbledon in the third round of the league cup and forth round of the FA Cup. The arrival of Gareth Southgate at Middlesbrough lifted the club in the summer of 2001 and the club saw a significant improvement in their performances, finishing the season off in 12th position. The highlight of their campaign came form reaching the semi finals of the FA Cup, losing their match against Arsenal in the last four.