12 Chelsea managers Arsene Wenger has faced in the last 21 years – #4 and #7 are his greatest enemies

2. Gianluca Vialli (1998-2000)

At 33 years old, Gianluca Vialli was still playing when he took over the managerial reigns at Chelsea, and in his two years at the helm he faced Wenger seven times. In fact, Wenger had much to do with the arrival of the Italian to the dugout. On October 8, his side beat Chelsea 2-0, and Gullit was sacked four days later. Up stepped Vialli, with a League Cup semi-final clash against Arsenal to look forward to just six days into his reign. You could have forgiven Wenger for expecting a victory. A league win just days previous, Chelsea in disarray… well, that certainly wasn’t the case. Patrick Vieira was sent off just after half-time, and the Blues stuck three past Alex Manninger to secure a victory.