Everton had a mixed season during their 1998-99 campaign, their league form was far from impressive as they finished off the season in 14th position, however they were unlucky in the domestic cup competitions. Everton met Sunderland in the last sixteen of the league cup, however they narrowly lost on penalties to the club. They put on a great run in the FA Cup and were most unfortunate to be defeated by eventual finalists, Newcastle, in the quarter finals. Everton narrowly lost the match 1-0 and were out despite a good performance. The following season saw little improvement for the Toffee’s, they were humiliated out of the league cup in the second round as they lost to lower league club, Oxford united. They were once again poor in the league, fortunate to finish off in 13th position. Once again they saved their best for the FA Cup, the only high point of the season was reaching the quarter finals, losing 2-1 to Aston Villa.
Everton saw no progress the following season as their league form dipped even further and was in a relegation battle for most of the season, managing to finish in 16th place. They were also poor in the cup competitions as they lost to their fellow Merseysiders, Tranmere, 3-0 in the FA Cup, a shock defeat. Worse was to come as Bristol Rovers beat them in the second round of the league cup.
The 2001-02 season once again provided little change for Everton, nothing was expected of them during the season and they did not please many of their fans. A dismal league campaign ended in them finishing in 15th position, making slightly flattering reading, judging by their performances. They however reached the quarter finals of the FA Cup, being beaten against Middlesbrough, a 3-0 thrashing.