The Frenchman this week marked 20 years in charge of the Gunners and it just so happens that his next match comes in the form of a London derby against the Blues.
It is apparent that Wenger has not enjoyed much luck against the West Londoners throughout his career and milestone matches in particular continue that trend.
Wenger's 1,000th match in charge of Arsenal resulted in a 6-0 hammering at the hands of the Blues in 2014, while his 500th match in 2005 saw arch nemesis Didier Drogba score in Chelsea's first win over their North London rivals in close to 10 years.
In recent times, Wenger has struggled whenever taking on the Blues who have a nine-game unbeaten run and are aiming for 10 without defeat on the weekend.
Also a stat to note is that Chelsea have won four times in the Premier League at the Emirates, which is more than any other side who has visited the venue.
So in short, Wenger will be hoping for a change of fortune on Saturday as he celebrates two decades at the helm of Arsenal.
Thanks to Chelsea's official website for the statistics and information.