21 Classic Arsenal vs. Chelsea Clashes | News, Scores, Highlights, Stats, and Rumors
Michael Green
Published Mar 24, 2026
Arsenal vs. Chelsea, Arsene Wenger vs. Jose Mourinho, these are some of the greatest rivalries the English game has ever seen. Over the course of 106 years and some 180 matches, the Gunners and the Pensioners have etched out one of the most contested clashes in football.
Their meetings now provide some of the most eagerly awaited Premier League matches in the calender.
Ask Wenger or Mourinho or any Chelsea or Arsenal fan who their main rivals are and neither name is likely to drip off the tongue first. While the North London derby between Tottenham Hotspur and the Gunners is obviously king in London, the rivalry between Arsenal and Chelsea is actually longer running and has been played across more games.
Arsenal and Chelsea first met each other on Saturday, November 9, 1907 when the Blues won 2-1. They last met on October 29 of this year in the Capital One Cup when Chelsea, once again, came out on top.
Including those two matches, the Pensioners and Gunners have met 180 times.
Arsenal's main rivalry against Spurs only began in the December of 1909, a full two years after the Gunners had met Chelsea. They have also only played each other 171 times in comparison.
In recent years, considering both teams' ambitions and aims and the fact that both are London's most successful teams, this is, perhaps, the biggest rivalry for each club.
Here, Bleacher Report takes a look through the great match history on show and offers up 21 classic games any discerning fan should know about.