These two sides have both won this trophy once each in their history, with Pompey lifting it as recently as 2019.
Match preview
After earning a respectable 0-0 draw at home against League One leaders Plymouth Argyle at the weekend, Bolton should head into their midweek cup tie against Portsmouth with plenty of confidence.
Indeed, Ian Evatt's side have now kept five clean sheets in their last six matches, with their possession-based style of play clearly frustrating opponents given that they have seen red cards shown against them in each of their last three games.
Having last won the EFL Trophy by beating Torquay United in the final in the 1988-89 campaign, which represents Bolton's last domestic cup triumph after narrowly missing out on the League Cup by losing to Middlesbrough in the 2003-04 final, Evatt will be keen to take the Trotters all the way to Wembley.
However, after failing to beat Portsmouth in either of their league meetings last season, the 41-year-old will know that his players will need to be close to their best if they are to prove successful on Tuesday.
Portsmouth, though, would consider themselves to be in the middle of a tricky period having failed to win any of their last five matches.
Their 3-1 defeat at home to Charlton Athletic last week saw Danny Cowley lose his job as manager after less than two years in charge of Pompey, with interim manager Simon Bassey performing well in his first game in charge to restrict Premier League opposition Tottenham Hotspur to a 1-0 win in the FA Cup third round on Saturday.
Bassey, who has never held a permanent managerial role before despite also temporarily leading AFC Wimbledon and Barnet in the past, will remain in the visitors' managerial dugout in Bolton on Tuesday as the club continue their search to name Cowley's permanent successor.
The 46-year-old will be hopeful of springing a surprise based on the evidence of his side's disciplined display at the Tottenham Hotspur Stadium at the weekend.
Bolton Wanderers EFL Trophy form:
W
D
W
W
W
Bolton Wanderers form (all competitions):
W
W
D
D
W
D
Portsmouth EFL Trophy form:
L
W
W
W
W
Portsmouth form (all competitions):
W
L
D
D
L
L
Team News
With both teams facing each other in League One four days after this cup fixture, both managers may not wish to show their full hand in a competition which they are likely to consider as less of a priority.
As such, Evatt may hand the likes of Josh Sheehan, Amadou Bakayoko, Elias Kachunga and Owen Beck an opportunity after the quartet came off the substitutes' bench during their side's draw against Plymouth last time out.
Portsmouth, meanwhile, are likely to make several changes, too, after expending plenty of energy to keep Spurs to only a one-goal victory in north London.
Joe Pigott, Ronan Curtis and Louis Thompson are three players expected to be named in Bassey's starting XI after appearing from the bench against Antonio Conte's side.
Bolton Wanderers possible starting lineup:
Dixon; Toal, Aimson, Johnston; Bradley, Morley, Dempsey, Beck; Sheehan; Bakayoko, Kachunga
Portsmouth possible starting lineup:
Oluwayemi; Swanson, Morrison, Raggett, Ogilvie, Hume; Tunnicliffe, Thompson, Morrell; Curtis, Pigott
We say: Bolton Wanderers 2-1 Portsmouth
We expect to see an entertaining encounter at the University of Bolton Stadium on Tuesday, with both teams likely to play with more freedom than they will in their forthcoming league meeting at the weekend.
Ultimately, though, Bolton are a far more settled unit under Evatt than their manager-less opponents, and should be able to squeeze out a victory as a result.