The AFC Telford United boss is a two-time Wembley finalist in the competition – the most recent ending in glorious penalty success and the first time ending in shootout heartbreak.
That debut final appearance, while manager of Wrexham in 2015, left a sore wound for Wilkin and one he was not able to heal, at least partly, until his Brackley Town success three years later.
The Red Dragons were overcome by North Ferriby United, of the tier below Wrexham, on spot-kicks after blowing a two-goal lead. Wilkin was axed from the Racecourse Ground less than 24 hours later.
Wilkin joined Brackley shortly after, amid Telford interest, and helped the Saints become one of National North’s most consistent outfits. They enjoyed huge national attention in 2018 by seeing off National League Bromley via penalties after a 1-1 draw.
Tomorrow Wilkin begins another journey in the competition as his AFC Telford side, bottom of National North, begin their campaign at the second round stage at Kings Langley, a Hertfordshire-based step three outfit, of the Southern Premier Central, the division below.
“Some good and bad!” Wilkin laughed when asked about his Trophy memories. “I’ve been lucky enough to win it.
“Unfortunately, I lost it on penalties with Wrexham and ended up losing my job the following day because of that.
“I went back there four years later or whenever and fortunately won it on penalties, I look back on that with a great deal of pride.
He continued: “Yes I would say it is probably up there, after the disappointment of losing when we were heavily expected to win, and the manner that happened.
“It was a difficult period there for me and my family, to be able to visit the place a second time, get through it, my family shared the success that day and squared the circle. It was fantastic, it is right up among my achievements so far.”
Telford have endured a number of national knockout cup woes over recent years. Last season Paul Carden’s side lost to step three Stourbridge in the Trophy. The Bucks exited the FA Cup to step four Chasetown this term.
There have been other dark days and forgettable defeats – to Stamford, Leiston and Nantwich – since the Bucks thrilled in reaching the Trophy last four against Leyton Orient under Gavin Cowan.
Wilkin said of Langley: “I went to watch them on Monday, whatever they put out we’ve got to adapt and deal with it.
“I’ve been a player and I didn’t like losing to an underdog, I didn’t like losing games, but if you’re expected to win – that’s the expectation on our players.
“It’s about being mentally capable to overcome the challenges on Saturday, they’ve got players in their ranks if you hand them moments and opportunities they’ll hurt you.
“We’ve all been on the end of them (upsets), they don’t feel great and they certainly wouldn’t feel great in the situation we’re in now.”
Midfielder Liam Nolan (calf) and Robbie Evans (chest) are doubts for tomorrow but Prince Ekpolo (bruising), Devarn Green (leg) and Harry Flowers should be available.“Liam Nolan still has a calf issue, I believe it is now, he was assessed at training and is highly unlikely to be available tomorrow,” the manager said.
“Prince has a bruise I expect him to get through and be available.
“Devarn Green had a dead leg and didn’t train Tuesday but we’re hoping that will settle down and he’ll be available.
“Robbie Evans has a bronchial infection, he didn’t train last night and becomes a real doubt for Saturday.
“Harry Flowers again didn’t train Tuesday but should be alright for Saturday.
“It’s more than we’d like but it is what it is, if somebody else gets a chance because of it they’ve got to step that chance.”