Kevin McNaughton reached the Premier League at the pinnacle of his playing career.
Now, as co-manager of Dundee North End, the former Scotland international is helping his club to scale new heights of their own.
Ex-Aberdeen and Cardiff City star McNaughton teamed up with former Dundee and United defender Lewis Toshney to take joint charge at North End Park in October 2022.
Since then, the City of Discovery-born pair have led the Dokens to the Quest Engineering Cup in 2023, followed by last season’s Midlands League title.
The club has long-term plans to move beyond the junior game into the professional ranks.
But for now, Sunday’s historic third round Scottish Cup tie against Airdrie has captured the imaginations of everyone connected with North End.
McNaughton fits his managerial responsibilities around studying to become a healthcare professional.
Marathon shifts at Ninewells Hospital are par for the course.
However, despite spare time being at a premium, the 42-year-old is relishing the challenge.
“I was college Monday, had an essay due Tuesday, a 12-hour shift Wednesday, Thursday and Friday. I don’t really get a break,” he explained.
“I’m a trainee assistant practitioner so I’m back at college. I’m a step down from a nurse.
“I’m in the acute frailty ward in Ninewells which is for the elderly. I do admissions which is quite fast paced and do a lot of testing on elderly patients.
“It’s a long way from football but I enjoy it. It takes its toll, especially these 12 hour shifts, but I enjoy working in the hospital.”
Last season’s title win secured North End’s place in the Cup and wins over Tayport, Tranent and Inverurie Locos earned them Sunday’s visit from Championship battlers Airdrie.
A bumper crowd will pack into North End Park for the lunchtime kick-off and, despite the four-division gap between the teams, McNaughton believes his side’s footballing approach – and strong home record – means they are capable of springing a surprise.
He said: “Just being involved in the competition is great for us. The guys have taken it proper seriously.
“Our main goal for the season is to try and win the league. This is that wee bit more special, with the prestige that goes with it.
“We’re playing at home as well. We had Tranent up, who are a very good junior team and we managed to get a really good result against them.
“We try and do things the right way. We play some decent football.
“I know Airdrie are the same. I’ve watched quite a lot of their games. They do actually play a half decent brand of football.
“They’ve struggled at both ends of the park really from what I’ve seen.
“We’ll go about the job the same way we’ve been going about it all season. We do try to play from the back and things like that.
“If you watch the game you’ll be surprised at how we go about things.”
McNaughton and Toshney’s links with Dundee ‘big two’ have helped them bring in the odd young player on loan and scoop up the cream of their released talent.
A priceless blend of youth and experience in the squad has helped the duo set high standards.
Come Sunday, the chance to measure themselves against Championship opposition will be a big motivator for North End.
McNaughton said: “Every season we’re just trying to make the club a wee bit better.
“Obviously things like the Scottish Cup, it’s a good showcase for us to see where we’re actually getting.
“This is where they step up. We’ve had a few friendlies against Forfar and Brechin and we’ve competed.
“I’m just hoping the boys turn up because they are capable of things.
“I’ve obviously played at a higher level – and there’s a few of them that could step up to seniors but it probably just doesn’t suit their lifestyle.
“It’s exciting. It feels like forever since the draw came up so I’m glad it’s here now.”
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