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

8. Carlo Ancelotti (2009-2011)

Carlo Ancelotti is a very successful coach, with three Champions League titles to his name, and major trophies in four different countries around Europe. And Wenger will be well aware of that, having been on the losing side three of the four times they met in English football. In the 2009-10 season, Chelsea struck five past Arsenal without reply, and the following season started much the same as Drogba caused Wenger yet more misery in October. Wenger finished with a flourish though, securing a much-needed win before Ancelotti left his position. It was the Emirates in 2010, just two days after Christmas, when Arsenal received a late gift courtesy of Alex Song, Cesc Fabregas and Walcott. Branislav Ivanovic pulled one back, but the points stayed safely in north London.