Not since Steve Morrow netted a Wembley winner past Sheffield Wednesday in 1993 have the Gunners lifted this cup, where their paltry return of two trophies comes in stark contrast to their record-breaking efforts in the FA Cup.
Mikel Arteta will hope to change that tonight with a trip across the capital, off the back of a fiery derby draw with Tottenham on the weekend.
Arsenal remain unbeaten this season but can not be said to have hit top gear yet, and a raft of fresh faces should get the chance to stake their claim against Brentford.
The Bees are certainly underwhelming compared to their previous selves. Injuries are catching up with Thomas Frank’s side and Kevin Schade is among those absent tonight after the 3-1 defeat to Everton last time out.
However, fans won’t be able to tune into this match on TV in the UK.
The Carabao Cup has an agreement with Sky Sports to show 15 games across the competition, with two per round at this stage. Instead of this fixture, Newcastle’s trip to Manchester City is live tonight after yesterday’s clash between Manchester United and Crystal Palace.
ITV1 will air a highlights show at 12.05am on Thursday morning after the game with the goals also available on the Sky Sports app and YouTube shortly after full time.
You can also follow the match live with Standard Sport’s live blog, featuring expert analysis from Simon Collings at the Gtech Community Stadium with kick-off at 7.45pm BST.