As a toddler aged three, Wilkie was playing with a ball in the hallway of his home when there was a knock at the door. It opened to reveal the figure of Jim McLean.
The former defender, a future servant of both of the city's senior clubs, was brought up a diehard United fan by his father Bruce, who went to games home and away, in Europe, the lot. Wilkie Snr had been angered enough by something to pen an angry letter to the club. Little did he suspect the legendary manager would arrive on his doorstep to talk it over.
Wilkie said: "My dad was a bit surprised that Jim McLean turned up at the house wanting to speak to him. I asked him about it a few months ago, because it just kind of popped into my head. He is maybe a wee bit embarrassed about it now."
After wholeheartedly making the transition to Dundee supporter during Wilkie's eight years with them, then reverting to type as Wilkie became a legend at Tannadice, these days Bruce will take more interest in the activities of junior outfit Dundee Violet than today's William Hill Scottish Cup quarter-final at Dens Park.
Wilkie Jnr, meanwhile, is ensconced as Stuart Garden's assistant manager at Montrose. But the tradition of free advice being handed over from the Wilkie household directly to the Tannadice boardroom remains to the present day. Wilkie, who shared a couple of Scotland squads with Jackie McNamara, gave the former Partick Thistle manager his wholehearted endorsement when he spoke to chairman Stephen Thompson prior to his appointment.
"I spoke to Stephen Thompson before he announced [McNamara], just to give my thoughts, and for what it is worth, I said I thought he is a good person and will do a good job," Wilkie said. "Most chairmen will ask people's opinions who have been around managers in the game. He probably didn't take too much notice of what I said but I suppose my opinion together with other people's might have made a difference. I didn't say anything negative about Steven Pressley, I think he would have been a good appointment as well. But Jackie has a lot of respect in the game and I think that will come across."
If the early signs at Tannadice indicate precisely that, Wilkie must also declare a personal interest in the events unfolding at Dundee. Although he wishes the incoming manager John Brown all the best, Wilkie was a team-mate of Barry Smith's between 1998 and 2006 and sympathises with the peremptory end to his friend's 17-year stint at the Dens Park to the extent that he has offered him the chance to remain in the game in an unofficial capacity at Montrose. "Myself, Stuart Garden, and John Sheran have asked Barry if he wants to get involved a little bit, if he wants to take a session or do a match report, just to keep his hand in," said Wilkie. "I think that is what he will do – just try to keep himself out the house as much as possible. The desire is definitely still there in Barry, he is a young manager and every single manager's cv has some disappointments on it."
After a 2-2 draw in a mini-Tayside derby against St Johnstone in midweek, today's real thing promises to be a huge game for Brown, whose appointment sparked a chaotic and conflicted response from the club's support.
"The board and the manager will both be desperately hoping they win the derby, because that will prove to the fans it will have been the right appointment," said Wilkie. "But if Dundee don't win it there could be major problems. I think the fans wouldn't be happy at all. But there is no way they could bring John in for that one game, then get rid of him if they lose it. They need to keep him until the end of the season now. I genuinely hope he does well, even though Barry is a close friend. These things happen. I just feel a bit sorry for him having to come into that situation. You wouldn't wish it on anyone coming into a new job."
"[Brown's appointment] just came out the blue so much. It didn't seem right that they said they had so many good candidates and then they gave the job to someone who has got a lot of respect and experience in the game as a player, but maybe not quite so much on the coaching side of things. It seems to be that the fans feel out of touch with the board, which is ironic because they have fans on the board. I do feel sorry for the Dundee fans because they need a bit of stability at their club and they haven't had that for years.
"I actually think Barry was achieving that in a sense, then getting thrown into the SPL disrupted it a little bit. He was preparing a team to win the First Division, but suddenly they were in the SPL, and that put a spanner in the works."
Wilkie intends to remain neutral today – he is hoping for a 2-2 draw – but considering his previous travails in this competition, cup glory for either club would be something to treasure. At Dundee, a tackle on his future team-mate Barry Robson caused him to miss out on a 1-0 Scottish Cup final appearance against Rangers: "It was an Amoruso header and I probably would have been picking him up," he jokes.
The boyhood United fan had to endure most of the club's infamous Scottish Cup final jinx and was posted missing as they finally lifted the trophy against Rangers in 1995. Come May 2010, when he was counting time on his career after a series of knee injuries, at least Wilkie had the privilege of lifting the trophy with Andy Webster when United finally prevailed against Ross County.
"Obviously you would have loved to have won it as a player, there would have been nothing better than that, but second best is what happened and I really appreciate everybody allowing me to do that.
"I never got a medal, but I wouldn't have accepted a medal being honest because I never took any part. There was a part of me that felt slightly embarrassed doing what I did, but I'm glad I did it, because if I hadn't I would have regretted it."