Dundee and Montrose, both already eliminated from the Scottish League Cup, will come together on Saturday afternoon for their final match in Group C.
The hosts took just three points from their three group fixtures, while the visitors have also managed only three points from three games.
Match preview
Dundee returned to the Scottish Premiership in 2023-24 and recorded a superb sixth-placed finish, but the Dee were unable to reach those same heights last term as they finished just four points above the drop zone.
Tony Docherty was dismissed following that disappointing campaign, with Steven Pressley brought in as his replacement - and the new manager made an encouraging start to life at Dundee.
The Dee won all three of their pre-season matches under Pressley, and the manager would have been hoping to maintain that form in his first competitive game in charge against Airdrieonians.
However, a 1-0 loss immediately piled on the pressure, and that only increased as Dundee fell 1-0 to third-tier Alloa Athletic on matchday two - a result that also confirmed their exit from the competition.
Pressley finally secured his first competitive win in charge as Dundee beat Bonnyrigg Rose 3-1 last time out, though it took two late goals in the final five minutes to prevent another underwhelming result against lower-league opposition.
Despite Dundee's elimination already confirmed as they trail the top two by six points, Pressley will be hoping for another victory - but more importantly, a significantly improved performance - ahead of their Scottish Premiership opener against Hibernian on August 3.
The hosts will be the favourites to claim all three points given their opponents, Montrose, compete in Scottish League One, but they have already struggled against lower-tier teams in their opening three games.
Montrose are in similar form to their hosts, as the visitors head into this one with three points from their three fixtures, having lost 2-1 to both Alloa Athletic and Airdrieonians, sandwiched around a 4-1 win over Bonnyrigg Rose.
While Montrose's elimination is also already confirmed due to taking only three points, Stewart Petrie will still be eager for a victory in their final match, looking to build a platform to build upon in their league campaign.
Montrose had a miserable 2024-25 season, dropping from fourth in 2023-24 to placing eighth and just four points above the relegation zone in League One, and they will be eager to return to the promotion battle this campaign.
Dundee Scottish League Cup form:
Montrose Scottish League Cup form:
Team News
Emile Acquah came off the bench and scored Dundee's second goal in their 3-1 victory over Bonnyrigg Rose last time out, and after helping spare Pressley's blushes, the striker could be rewarded with a start.
The striker is likely to partner Simon Murray and Drey Wright in attack, while the rest of the starting team could remain the same from their recent win.
As for Montrose, Ewan Loudon has scored two of their six goals in the group stage, and the striker is likely to start alongside Craig Wighton.
At the other end of the pitch, Kieran Freeman, Andrew Steeves, Aidan Quinn and Kerr Waddell could continue in defence for the visitors.
Dundee possible starting lineup:
Carson; Astley, Koumetio, C Robertson; Ingram, Digby, F Robertson, Garza; Wright, Acquah, Murray
Montrose possible starting lineup:
Clark; Freeman, Steeves, Quinn, Waddell; Shrive, Masson, Webster, Brown; Loudon, Wighton
We say: Dundee 2-0 Montrose
Dundee have struggled in their initial competitive matches under Pressley, but a first win under the new boss may boost their spirits, and with a return to their home ground for this game, we believe the hosts will manage to secure another victory.
For data analysis of the most likely results, scorelines and more for this match please click here.
No Data Analysis info