The former Doncaster Rovers and Burton Albion player worked in a sweet factory before moving to Eastwood Town as a trainee, where he once scored four goals in an FA Cup tie against Crook Town.
Now a manager, Kirkwood leads his side into a Preliminary Round tie against Thurnby Nirvana on Friday night with a place in the First Round Qualifying at stake.
Mickleover Sports v Thurnby Nirvana
The FA Cup
Preliminary Round
7.45pm, Friday 29 August 2014
Raygar Stadium, Mickleover
Winning club will receive £1925 from FA prize fund
Kirkwood's affinity with The Cup has not stretched beyond a couple of Second Round appearances during his days at Doncaster, with the bricklayer just falling short of a mouthwatering clash with Leeds United in 1999.
He said: "We just missed out in a Second Round replay against Rushden & Diamonds. I don't think I've ever cried as much in my life.
"It's a massive game for the club and the players. I'm an old romantic, and for me The FA Cup is the best cup competition in the world. This is a brilliant game for us, and we're really looking forward to it.
"It's massive for the club financially, but as a club and as a manager, you want to test yourself against higher teams, and you want to see how far you can progress – that means getting to the Second or Third Round.”
He added: "Every non-League club's aim is to try to get to that First Round.
"We had a good season last year, and we've started OK this year. We've had Thurnby watched twice already this season, but we've had previous games against them, and it's never been easy. It's always very physical, so hopefully our lads will be up for it and be able to get us through."
Mickleover's home matches are currently played on Friday nights due to the club sharing the same ground with the local cricket team during August, but Kirkwood is hopeful that the prestige of The Cup will draw a good crowd.
"It's not ideal, but obviously with Derby County and Burton Albion just round the corner, hopefully a few of their fans will turn up just like they did last time we played on a Friday earlier on in the season. The Cup is such a big competition - it gets people dreaming."
Mickleover, currently ninth in the Northern Premier League Division One South, enter at the Preliminary Round stage and Kirkwood has called on his players to take full advantage of the extra attention a good run would bring.
"We have a lot of players from Step Five, but apart from one, who has been a pro for years – Chris Palmer – we've got a young squad without any Cup experience. They will be extremely eager to create memories," said Kirkwood.
"We are always looking to improve. We were unlucky to lose in a play-off final last season, and the chance to move up to step four.
"There's a lot of work that goes on behind the scenes of what is a really family-based club. We're proud to be part of the village and if we can help put Mickleover on the map with a good cup run, it would fill us with immense pride."
