He is now back with Sutton United, hoping to repay the helping hand they gave him 16 years ago when the non-leaguers rescued him from the prospect of life on football's scrapheap.
That act of faith in a boy rejected by his childhood favourites at Fulham persuaded Gordon Strachan to pay £1.5million to take him to Middlesbrough from Charlton when they were one of the top dogs in the Championship.
Life has turned full circle for Bailey now, and he's back where he started. But he'll never forget those three years in the big time, and the part Sutton played in him getting there.
That's a major reason Leeds United had better watch out if they turn up less than fully focussed at the National League side's little Gander Green Lane ground where Sutton knocked high flying Coventry out of the FA Cup 28 years ago.
Nicky Bailey started his career at Sutton
Sutton beat AFC Wimbledon in the last round
"I am playing against Leeds in a team that means a lot to me," says Bailey. "Sutton gave me a chance to make it in the game when I was just 16 and helping my dad at the fruit and veg market.
"I have played against Leeds a few times in my career, and we will be looking to give them a good game on Sunday – and we will. We have nothing to lose.
"They won't be used to the pitch (artificial) and we will make it as uncomfortable as we can for them.
"No team will ever bully us. Many have tried and failed. We know Leeds are a big strong team, but we can match them in that department."
Fighting talk from a player who would love to deliver a knockout blow to Leeds and set Sutton up for a massive fifth round pay day.
Sutton host Leeds tomorrow in the FA Cup fourth round
"It's going to be tough," he admits. "But it's still just 11 against 11. I have played against these players before and beaten them before.
"We know that on this pitch we are a good team and will give them a good game. We know they are good players. We know Chris Woods has got a lot of goals and will be their main threat, but we have to deal with that.
"They are in the Championship, we are in the National League training twice a week and with some players who will probably have to work on Saturday to get a bit more money in their pockets," he revealed.
And it's those same players who Bailey reckons are good enough to pull off an upset today.
"They are good players. No professional footballer likes dropping down because they think they are better than that. This is their chance to show they are.
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"We have Craig Eastmond,who played for Arsenal as a kid, and Roarie Deacon, who was also at Arsenal as a youngster. He has been our magic man, as they say, getting all our vital goals.
"These players are more than capable to be pushing for League One or the Championship, and it's is a great showcase for some of them. If they can perform against a Championship team maybe someone will take a gamble on them."
Bailey, now 32, isn't giving up on the future either.
When he returned to his roots last January Sutton were 12th in the National League South. "But we went on a run of 26 games without defeat and won the league by six points,`' he recalls. "And I know I could step up and play at a higher level again."
Bailey admits that if he hadn't been facing Leeds today he would have been at Craven Cottage with his dad watching Fulham play Hull City.
And if Sutton do produce one of those FA Cup giant killings father and son will be celebrating together in Sutton's clubhouse – just like they did after beating Wimbledon in the last round.
"We came back with all the fans and some of us were there until 5 in the morning," he added. "You can afford to be a bit more laid back at this level."