Remarkably the Gunners boss has never gained the upper hand over his Portuguese counterpart, drawing four and losing five as they prepare to do battle on Monday nightArsenal will be looking to regain top spot in the Premier League with victory over Chelsea on Monday.
Liverpool replaced Arsene Wenger's men as league leaders on Saturday courtesy of a 3-1 victory over Cardiff City, while Manchester City climbed into second by beating Fulham 4-2.
Arsenal can move back to the summit with victory over Jose Mourinho's men, but defeat would see them slip to fourth with Chelsea moving level on points with the Merseysiders.
|4/1||Arsenal are 4/1 wiith bet365 to lose to Chelsea by one goal|
Last season's two league clashes ended 2-1 in favour of the men from Stamford Bridge, who also won a League Cup fourth-round meeting at the Emirates Stadium 2-0 earlier in this campaign.
Arsenal lost 6-3 to Manchester City last time out, but have not suffered a home top-flight defeat since the opening day of the season.
Chelsea will be keen to rediscover their best away form, which eluded them in a 3-2 defeat to Stoke City a fortnight ago.
Mourinho is expecting a tougher challenge than his side faced in October's cup clash.
"It's a different competition, with different motivations, different responsibilities, and, in some cases, different players," he said.
"It's a big match for sure. It's still a London derby; it's still Arsenal and Chelsea.
"I'm ready for the game; I'm waiting for the game and I very much want to play the game."
Arsenal will be without the suspended Jack Wilshere, who is serving the first instalment of a two-game ban for making an offensive gesture to Manchester City fans last weekend.
Wenger knows his side must adapt to cope without the midfielder.
"[Wilshere] was wrong in his reaction; we just thought it was a one-game ban and that's why we appealed but we are now in a situation where we have to accept it and wait until he comes back, and focus on our next games without him," Wenger said.
Laurent Koscielny is unlikely to feature for the hosts after suffering a gashed knee against City, but Lukas Podolski is available to make his return from a hamstring problem.
Alex Oxlade-Chamberlain and Abou Diaby (both knee) remain sidelined.
Chelsea have no fresh injury concerns, but Mourinho has confirmed Ashley Cole will not start against his former club.