4. Jose Mourinho (2004-2007; 2013-2015)
In 15 clashes with Mourinho, Wenger won just one. A rivalry that has spanned decades, a war of words that still drags on to this day with Mourinho in charge of Manchester United. Just this week, Sportsmail revealed new quotes from Mourinho in which he claimed: ‘I will find him one day outside a football pitch and I will break his face.’ That said, our focus is inside the football pitch, and on Wenger’s incredible 6.7 per cent win record over Mourinho at Chelsea. The first time they locked horns was in Chelsea’s title-winning season, when Arsenal finished runners-up but still managed to lift the FA Cup.
They drew twice that season, but things took a turn for the worse in 2005-06 when Chelsea beat Arsenal in the Community Shield (a 2-1 win with Didier Drogba scoring both), before going on to two impressive Premier League triumphs. That season, Chelsea won the title again, Arsenal scraped to fourth, and the rivalry intensified. Mourinho left Chelsea in 2007 for pastures new, but returned in 2013 to reignite the fire. You will remember the famous handbags moment on the touchline as the pair pushed and shoved each other. That was October 2014, a 2-0 win for Chelsea. There was also an incredible 6-0 Chelsea win in March of the same year, yet another Mourinho victory over his old foe. In fact, the only time Wenger got one over on Mourinho the Chelsea manager was last year, the 2015 Community Shield. The Frenchman swerved his old enemy’s handshake, before Alex Oxlade-Chamberlain secured a sweet, sweet victory.
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