The tie of the round sees Arsenal make the short trip to White Hart Lane for the first North London derby of the season - and whilst it is only in the Capital One Cup, there is plenty riding on the game.
Spurs head into the game having won three on the bounce in all competitions, with Sunday's 1-0 win over Crystal Palace handing Mauricio Pochettino his first home league win of the campaign.
However, Arsenal not only lost 2-1 to Dinamo Zagreb in the Champions League last week, but were also beaten 2-0 by Chelsea at Stamford Bridge on Saturday.
A third defeat in a row - and to their biggest rivals - would pile pressure on manager Arsene Wenger, with a place in the next round as well as bragging rights on offer.
Now, former Arsenal midfielder Paul Merson has told Sky Sports that he believes the game will go to extra time after a 1-1 draw at White Hart Lane - but has backed the Gunners to edge Spurs out in extra time and take their place in the next round.
"It doesn't get any bigger than Wednesday night, despite the competition, and I hope Wenger treats it that way - if Arsenal lose this game then he's under a bit of pressure," said Merson. "It really is a very big match and has really given a boost to the Capital One Cup," he added.