It was maybe written in the stars that the one who got away would send Dundee crashing out of the Betfred Cup.
Lawrence Shankland caught Neil McCann’s eye over the summer as the Dark Blues’ boss searched for someone to score goals.
The deal was never done, though, and the Ayr United forward duly showed McCann what he has missed out on when he smashed a shot home on 51 minutes to put the Honest Men 1-0 up in their last-16 clash at Dens.
As if to rub McCann’s nose in it, another striker who has been the biggest culprit in missing chances, substitute Sofien Moussa, was only on the pitch for 15 minutes before he was sent off for two quickfire bookings.
Man-of-the-match Shankland then had a fair number of Dundee fans heading for the exits when he made it 2-0 with just four minutes to go.
The seats were almost empty on 88 minutes as Michael Moffat slid the ball home from just a yard out to make it 3-0 to Ian McCall’s team. The red card count then went to two when Dundee defender Genseric Kusunga was sent packing for a foul on Moffat.
It was a comfortable and richly deserved victory for the visitors, who had had the better of the first half and probably felt unlucky to be goalless at the break.
Dundee brought new Finnish frontman Benjamin Kallman off the bench for the second period.
However, it was Shankland who brought the match to life with a fine finish.
Moussa then had his two moments of madness after replacing Jean Mendy on 63 minutes.
Firstly, he was booked for a challenge on Andy Geggan then he fouled Mark Kerr and it was game over for him and McCann’s side.
Ayr were in control by then anyway and it was no surprise when Shankland side-footed home from close range and then Moffat bagged the third.
The dismal result piles some early-season pressure on the Dark Blues and ensures that, once again, they miss out on a decent cup run.