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

3. Claudio Ranieri (2000-2004)

Wenger has only faced Jose Mourinho more times than Claudio Ranieri in his clashes with Chelsea over the years. The now-Leicester manager came up against the Arsenal boss 14 times in his four seasons at the Bridge. Their first league clash – in January 2001 – saw the two sides share the spoils as a 20-year-old John Terry netted a second-half equaliser. They faced each other once more that season, in the fifth round of the FA Cup, and Arsenal ran out 3-1 winners on their way to the semi-final of the competition. Wenger got the better of Ranieri on many an occasion, only losing once in their 14 clashes. That said, he would no doubt swap all of that for another little taste of the title, just as the Tinkerman did with Leicester last season.