Pompey open their EFL Cup campaign with a trip to League One outfit Coventry this evening (7.45pm kick-off).
They shocked second tier Derby at this stage of last season’s competition before narrowly falling to Reading at the next hurdle.
Tonight’s opponents, meanwhile, lost on penalties at Rochdale 12 months ago and have not won a tie since 2012.
Both sides are searching for their first win of 2016/17, with Pompey drawing 1-1 against Carlisle on Saturday and Coventry losing at Swindon.
The sides have not met competitively since they were both in League One four seasons ago.
Jed Wallace and Patrick Agyemang were on target in a 2-0 Blues victory at Fratton Park, while Izale McLeod salvaged a late draw at the Ricoh Arena.
Pompey fans will have fond memories of an FA Cup third round replay back in January 2010, when Aaron Mokoena scored a winner right at the end of extra-time and the team went on to reach the final at Wembley.
Pompey are expected to make wholesale changes to their side, with Adam Buxton, Curtis Main, Amine Linganzi (subject to international clearance) and Liam O’Brien hoping to make their debuts.
Matt Clarke (groin) and Brandon Haunstrup (collarbone) are both out, while Ben Close (hamstring) is also a doubt.
Read what Paul Cook and Adam Barton have to say about tonight’s game or watch video interviews on Pompey PlayerHD.
HEAD TO HEAD
Pompey: 11 Wins
Coventry: 14 Wins
Pompey: 3 Wins
Coventry: 10 Wins
Tickets are no longer available to buy from Pompey and will not be on sale to visiting fans at the Ricoh Arena tonight.
Pompey PlayerHD subscribers can listen to live commentary from the Ricoh Arena from 7pm tonight.
We’ll also have match updates on Twitter and our Pompey Wall feed on the club website.
There will be post-match reaction on the website, Pompey PlayerHD and our official YouTube channel, with highlights to follow on Wednesday.