Fighting to climb off of the foot of the Group C table in the Scottish League Cup, the Lowland League's Bonnyrigg Rose Athletic will face Premiership club Dundee at Ferguson Park on Tuesday.
The Rose will be hoping to bounce back from three straight defeats in midweek, while the Terrors will be looking to avoid building a losing streak of their own.
Match preview
Jonathan Stewart's Bonnyrigg Rose are in dire form ahead of this clash, and having lost four and drawn one of their last five games across all competitions, they will be low on confidence.
On Saturday, the Rose were thrashed 4-1 by Montrose in the cup, and while the result was not unexpected, the manager will be disappointed that his team took the lead through Kallum Higginbotham only to concede four without reply.
That defeat left Stewart's side rooted to the bottom of table with zero points, six behind second-placed Airdrieonians, and their minus seven goal-difference is by far the worst in the group.
If the hosts are to turn their fortunes around in midweek, then they will need to defy their shocking home record that features only one victory - alongside two draws and six defeats - across their last nine matches.
Three points would be enough to see Bonnyrigg Rose leapfrog their opponents and climb up to fourth, but their goal-difference is likely to stop them from overtaking Montrose.
Meanwhile, Jim Goodwin's Dundee have also made a poor start to the 2025-26 domestic calendar by losing their opening two Scottish League Cup games.
This past weekend, the Terrors followed up their 1-0 defeat against Airdrieonians by losing 1-0 to Alloa Athletic, and while they walked away empty-handed, fans may take heart from the fact that both scorelines were narrow.
On the other hand, Goodwin's men failed to score in either game, and are now only being kept from the very bottom of Group C thanks to their hosts' porous defence.
Hoping to finally put points on the board, the visitors' travelling record that includes four wins from their six most recent away clashes suggests that they could gain ground on their rivals in midweek.
A first cup victory of the season could take Dundee level on points with Montrose on Tuesday, and they might even end up in third place if they can benefit from a four goal-difference swing.
Bonnyrigg Rose Athletic Scottish League Cup form:
Bonnyrigg Rose Athletic form (all competitions):
Dundee Scottish League Cup form:
Dundee form (all competitions):
Team News
Aiming to get off the mark against the odds, Bonnyrigg Rose should start Cameron Ross up top, flanked by Kallum Higginbotham and Rudi Bryce.
In the centre of the park, Stewart is likely to turn to the trio of Max Dowling, Billy King and Kian Speirs to try to secure stability in midfield.
As for Dundee, Goodwin will be hoping that his frontline of Emile Acquah, Tony Yogane and Simon Murray can find a breakthrough after blanking in consecutive matches.
At the opposite end of the pitch, centre-back Luke Graham will be trying to make up for his own goal against Alloa, while full-backs Plamen Galabov and Imari Samuels offer overlapping runs out wide.
Bonnyrigg Rose Athletic possible starting lineup:
Connelly; Young, Fellows, Martyniuk, Sommerville; King, Dowling, Speirs; Higginbotham, Ross, Bryce
Dundee possible starting lineup:
Carson; Galabov, Donnelly, Graham, Samuels; Robertson, Wright, Digby; Yogane, Acquah, Murray
We say: Bonnyrigg Rose Athletic 1-3 Dundee
Both teams may be on zero points so far, but Bonnyrigg Rose are undoubtedly the underdogs, and they will be hard-pressed to avoid a fourth defeat.
As for Dundee, coming up against the most fragile defence in the group could be the perfect opportunity to get back into goalscoring form.
For data analysis of the most likely results, scorelines and more for this match please click here.
No Data Analysis info