It wasn’t looking good for a while with Airdrieonians recovering to make it 2-2 having already lost an early lead established through Calum Gallagher's fine strike after 21 minutes. The hosts had seemingly taken charge after going in front after goals either side of half-time from Paul McMullan and Zak Rudden, both stemming from errors by Airdrie goalkeeper Dean Lyness.
The second was particularly catastrophic although Rudden still had much to do after the ‘keeper failed to deal with a long ball outside his box.
Dundee, whose only Scottish Cup triumph was in 1910, have a habit of making heavy weather of such appointments against lower division opponents. Although the eventual 6-2 scoreline might indicate otherwise, it was a familiar tale here once more.
Callum Smith slammed in an equaliser after 65 minutes following a fine through ball from ex-Dundee United man Charlie Telfer.
“Ladies and gentlemen, there will now be 30 minutes of extra time,” confirmed the Tannoy announcer. This was clearly news to some in the main stand. Many had already started shuffling towards the exit. There was even some booing at the mistaken prospect of a midweek trip to Airdrie for a replay.
Instead, Dundee had another half an hour to find a way past their redoubtable opponents. Even better, they were seeking to do this against ten men. Cameron Ballantyne was shown a red card in time added on at the end of 90 minutes for a second bookable offence after he brought down Dundee substitute Alex Jakubiak in the middle of the park. It was arguably the defining moment.
Another substitute, Deryk Osei, finally scored 13 minutes into the first half of extra-time. Jakubiak’s shot on the turn was well saved by Lyness and Osei was on hand to force the rebound home. Osei scored again shortly after the re-start before Finlay Robertson, yet another substitute, scored his first goal for the club with a well-controlled finish from just inside the box.
It clearly meant a lot to the 20-year-old Dundee supporter, who made his debut as long ago as 2019. Luke McCowan – yes, you guessed it, another replacement – wrapped things up with a sixth shortly afterwards. It was a result that had barely looked possible not such a long time beforehand.
Home goalkeeper Ian Lawlor was forced off in the second half after a brave save to stop Smith’s seemingly net-bound header saw him hit his face against the post.
Dundee survived but Lawlor exited to be replaced by Adam Legzdins. The injured ‘keeper left hoping his side had it in them to take command of the tie once more. A team from the third tier taking the game to a team from tier above after half time had not been in the script.
Airdrie’s fitness levels were exceptional though they understandably wilted in extra time, when a player short. Their fans gave them a rousing reception at the end. It was deserved.
Airdrie will rue not being quite able to reach half-time of extra-time still on level terms. Dundee closed out the win with Osei scoring again three minutes after the re-start after taking a touch and then turning in a cross from McCowan. Further goals from Robertson and McCowan safely deposited Dundee in the next round.