Dundee moved top of Group C after a hard-fought 2-0 win at League One Montrose.
Despite creating a host of chances and striking the woodwork three times, the Dark Blues had to wait until the 70th minute to break the deadlock.
It was two substitutes who did the damage as Luke McCowan netted two minutes after Jason Cummings opened the scoring from the spot.
Victory sees the Dark Blues all but through to the knockout stages with nine points to their name ahead of Saturday’s home clash with Forfar.
If it ain’t broke…
Dundee boss James McPake took the if-it-ain’t-broke-don’t-fix-it approach to team selection, naming the same side that beat Brora Rangers 4-0 last week.
The only change to the matchday squad was new signing Ian Lawlor taking a place on the bench. Cillian Sheridan’s international clearance is yet to come through, denying him the chance of a debut.
The hosts, meanwhile, had former Dees Kerr Waddell and Matty Allan in their line-up as Stewart Petrie made five changes.
In for the Gable Endies were Allan, Lewis Milne, Craig Brown, Alan Fleming and Graham Webster.
Away fans return
Dundee fans hadn’t enjoyed an away day since March 7, 2020, and a drab 0-0 draw in miserable weather at Ayr United.
Fast forward 16 months and Dees were back on their travels in full voice, with around 600 enjoying far more clement weather in Montrose.
The first half took a little while to warm up, though.
Eventually the Dark Blues began to test the home defence with skipper Charlie Adam making his influence felt.
First he had a couple of efforts – a free-kick on target before heading a Jordan McGhee cross over.
Then he turned provider, sending in a corner for Liam Fontaine to crash a header off the bar on 27 minutes.
A superb throughball then found Jakubiak but his headed effort from the bouncing ball was beaten out by the goalkeeper before Fontaine flashed another header wide.
On the cusp of half-time, Dundee hit the bar once more, this time Lee Ashcroft heading an Adam corner onto the frame of the goal.
Quickfire double
After the break the chances kept coming but still the opening goal wouldn’t arrive.
Paul McMullan had the first effort of the second period, seeing a deflected volley well saved by Fleming in the home goal.
The home side were also showing more of a threat with a good defensive header from Ashcroft dealing with a dangerous Liam Callaghan delivery.
On 64 minutes, McMullan showed his trickery, working his way into the Montrose area but poked his effort wide of the post.
Finally the elusive opening goal came as Jordan Marshall was brought down in the area by Graham Webster.
Up stepped substitute Jason Cummings to stroke the ball into the corner from the spot to open his account for the season.
And it was 2-0 just moments later with another subbie on the mark for the visitors.
Fleming did well to save Jordan McGhee’s low effort but could only palm it straight to McCowan to slam home, grabbing his first goal for his new club.
Up the other end, Dundee almost made trouble of their own making as goalkeeper Adam Legzdins misjudged a bouncing ball.
That gave Blair Lyons an open goal from an angle but he was denied by a last-ditch saving challenge from Ashcroft.
Cummings almost grabbed himself a second goal but saw a low effort come crashing back off the post.
Dundee finished the match with 10 men, however, as McMullan limped off in the closing stages following a hefty challenge.
Teams
Montrose: Fleming, Allan, Steeves, Dillon, Waddell, Masson (Rennie 80), Webster (Watson 73), Callaghan (Lyons 63), Brown (Johnston 63), Whatley, Milne (Antoniazzi 73).
Subs not used: Garnham, Lennox.
Dundee: Legzdins, Kerr (Elliott 46), Fontaine, Ashcroft, Marshall, Byrne, Adam (Anderson 63), McGhee (Robertson 83), McGowan (McCowan 63), McMullan, Jakubiak (Cummings 46).
Subs not used: Sweeney, McDaid, Panter, Anderson, Lawlor.
Referee: Alan Newlands