The 1994- 95 season saw the arrival of new player manager, Glenn Hoddle at Stamford Bridge. The Blues were looking to build on their 14th position finish the previous season. They finished the campaign off in an improved 11th place. Chelsea strengthened their side at the start of the campaign; bring Paul Furlong in from Watford. They could only manage to reach the fourth round of the FA Cup suffering defeat on penalties against Millwall.
The 1995 -96 league season was similar in comparison to the previous year as the Blues finished it off in 11th position. They did enjoy a fine run in the FA cup, reaching the semi finals of the competition, suffering defeat against Manchester United in the last four in a match played at Villa Park. Mark Hughes and Ruud Gullit signed for the blues at the start of that season. Many players were in fine form for the blues during the 95- 96 season, including, Mark Stein, Craig Burley, Steve Clarke, Gavin Peacock, Nigel Spackman, Scott Minto, Frank Sinclair and Dmitri Kharine.
Ruud Gullit was appointed player manager of Chelsea at the star of the 1996- 97 season and the response was immediate as the blues enjoyed a nice league season, finishing off in a much improved sixth place. Gianluca Vialli, Roberto Di Matteo, Dan Petrescu and Frank Leboeuf all joined the Blues at the start of the season. Chelsea enjoyed a delightful run in the FA Cup, progressing into the final, meeting Middlesbrough there. Roberto Di Matteo scored for the Blues as they won the encounter 2-0.
There was a lot of change in the Chelsea side during the 1997 -98 season as they brought in more new talent, including Celestine Babayaro, Gustavo Poyet and Ed De Goey. The Blues reached the final of the league cup, meeting Middlesbrough once again in a cup final and once again beating the club 2-0.