#4 Roberto Di Matteo
Although Di Matteo is known more for his Champions League triumph as the Chelsea manager, he had quite a decent time in the Premier League as a player. The Italian made an instant impact by scoring the winner against Middlesbrough on his home debut. The midfielder would later go on to make 119 appearances for the Blues where he scored 15 goals and set up 13 for his team as well.
Di Matteo arrived at Chelsea from Lazio in 1996 and spent over six years at Stamford Bridge. His passing ability and precision as a long distance shooter saw him become an integral part of the Blues squad over the years that he played at the club. Chelsea finished its highest since 1989-90, in the 1996 season when Di Matteo arrived as they ended up at 6th on the table.
