But the one-time poster boy for Northern Ireland football actually turned 38 on Monday and has now made the decision that this coming season with Longford Town will be his last in the game.
“As you get older you struggle to get over games more than when you are younger,” he says. “And I thought that in another year the body will be aching even more. It’s different now than when I was playing full time and training every day. I don’t have that, so it’s difficult to stay in peak condition and that was part of the decision.”
He admits there were lows as well as highs over the course of his football life — not least the gambling problems about which he has spoken in the past — but the happier memories are sure to sustain him in his retirement.
“The best time of my career was at Newcastle,” he says, citing in particular the unforgettable, if bittersweet, 1995/’96 season when, having been front runners in the title race for most of the season, the Magpies had their wings clipped by Manchester United at the death. “We didn’t win the league but everyone remembers the team I played in. Not many people remember the team that came second two years ago but everyone remembers that Newcastle team, and that was due to the style of football we played.
“I played 86 times for Northern Ireland — that was a big thing. And I have played for big clubs and big name managers — Ferguson, Keegan, Dalglish, Guillit. I learned a lot from them.”
As he contemplates his own retirement, the remarkable fact is not lost on Gillespie that Alex Ferguson — who already had five years on the clock as Manchester United manager when the player signed for them in 1991 — is still at the helm at Old Trafford.
“It’s crazy to think that it was five years ago when he was going to call time on it,” he says. “He just lives and breathes football. And when you have built up something so successful it’s hard to walk away. Nobody would question it if he did, but he has that hunger to win trophies and while he has that he will keep on going.”
Looking back on his own career, Gillespie doesn’t hesitate when asked to nominate a stand-out game.
“Against Barcelona, for Newcastle in the Champions League, playing against Figo and Rivaldo, and we won 3-2. That was probably the best game I ever played [Gillespie laid on two goals for hat-trick hero Faustino Asprilla]. That was in 1997 but Newcastle fans still remind me of it to this day.”
And, lest we forget, there were a few wonderful nights in the green of Northern Ireland to cherish too. “We beat England [1-0 in 2005] which was a big thing as nobody gave us a chance and then a year later we beat Spain 3-2 at Windsor. The team we beat went on to win Euro ’08 and had all the big names playing that night.”
However, it’s south of the border where he will hang up his football boots after his surprise move to Longford Town in 2011. But if anyone thought it was just a cosmetic exercise to try and attract some publicity on the back of a fading star, Gillespie’s performances in a new central midfield role for Longford last season — which ended with him being named in the First Division team of the year — would have made them think again.
“I’ve heard about people coming here and maybe not taking it too seriously, but as a sportsman you want to give it your all,” he reflects. “It’s difficult as I played in some big stadiums all over the world, and the First Division is a culture shock, but you get used to it. Playing in stadiums where you can’t swing a cat in the changing rooms. Subs having to go out while the team changes. But it’s part of football and I’ve still enjoyed it.”
Longford have announced a new shirt and naming rights deal with international recruitment company City Calling, which will see Flancare Park renamed the City Calling Stadium for, at least, the next five years. And with manager Tony Cousins expressing confidence that things are progressing nicely on the pitch too, there’s a growing belief at the club that this could be the season when Longford finally return to the Airtricity League Premier Division.
And don’t be too surprised either if, by year’s end, their best-known player is tempted to reverse his decision to retire.
“At the minute my mind is made up but I may revisit it,” Gillespie smiles. “But it would be nice to go out on a high and achieve promotion. We looked like doing it for long periods last year but unfortunately we came up short. Tony has new players and a good squad now and we really feel this could be the season.”