Colchester United head to the south coast in search of three points to get their 2020/21 EFL Trophy campaign off to a good start.
It will be another tough game for Steve Ball and his team against a strong League One side that have qualified for the play-offs in the last two seasons, and will be looking to go one better this season.
Pompey are also recent winners of this competition, having lifted the trophy under the arch at Wembley in 2019 with a penalty shoot out win against Sunderland. They also progressed to the final of the competition last season before the Coronovirus pandemic brought a halt to proceedings. It is still undecided as to whether their Wembley date with Salford will still go ahead.
The hosts for Tuesday evening's match are managed by former Watford and Wales defender, Kenny Jackett, who has been in charge at Fratton Park since taking over from Paul Cook in the summer of 2017.
Like the U's, Portsmouth have only played one game this season - an entertaining 3-3 draw against League Two opponents Stevenage in the first round of the Carabao Cup. After being two goals down in the opening ten minutes, Pompey managed to draw level just after half time thanks to goals from Ronan Curtis, Gareth Evans and John Marquis.
Pompey eventually progressed through to the second round after a penalty shoot out where 'keeper Craig MacGillivray saved three from four Stevenage attempts.
After the game, Jackett was pleased with his teams comeback after a poor start:
"We have to start better than that because we gave ourselves a mountain to climb, although the fact we ultimately went through shows our character."
The U's will be looking to take positives from Saturday's 3-1 defeat at Reading. It was a first half performance to be proud of the the U's taking the lead through a Jevani Brown goal.
But United were unable to keep out their opponents, as Lucas Joao headed his side level in first half injury time. Joao turned out to be the match winner with a further two goals in the second half that eliminated United, but Steve Ball was still pleased with his side's performance.
"I was delighted with the first half. I think that we were up against a really good side in Reading, who have got some really good players.
"The way we took the game to them - some of our one touch play in the first half meant we have really good opportunities to score. If we'd have gone in 1-0 up at half time, I think that would have been deserved in some ways, but then we conceded a goal from a far post header.
"I was really, really happy with that performance."
You can watch all the action as it unfolds at Fratton Park with a £10 match pass by clicking HERE.
For help on how to purchase a match pass, click HERE.