9. Ruud Gullit (Chelsea, 1998):
Unlike under De Matteo, Chelsea were flying high under Guillit back in 1998. After landing Chelsea the FA Cup, the previous season, he took the club to the League Cup semi-finals and the Cup Winners Cup quarter-finals while also taking them to the second place in the points table. However, he got sacked under circumstances that were never explained. Gianluca Vialli took over and won both the cup competitions that year.