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Match preview
A repeat of the 2008 FA Cup as these two clubs meet again, albeit in a slightly less high-pressure fixture.
Back then, Nwankwo Kanu poked home the only goal of the afternoon as Portsmouth prevailed 1-0 at Wembley.
Who will win this time?
Safe to say, a lot has happened to Pompey subsequently.
The following November, they played A.C. Milan in the UEFA Cup but then almost went bust and suffered three relegations in four seasons.
These days, under Danny and Nicky Cowley, Portsmouth are in League One, starting the season with back-to-back draws, 3-3 with Sheffield Wednesday and then 0-0 with Lincoln.
The Bluebirds beat Norwich City on opening day but were then beaten 2-1 by Reading on Saturday.
In League Cup terms, Cardiff were runners-up in 2012, beaten by Liverpool on penalties, but have only won one of their last six ties.
Who will get through at the Cardiff City Stadium?