He began his schoolboy playing career in the early 80's with Stella Maris, before being signed by his local Leinster Senior League club, Fairview CYM – then managed by his father. From there, Gill, along with his brother Mark, moved to Home Farm F.C. in 1986 after being spotted by Ray Treacy in the Oscar Traynor competition playing for Fairview against the Athletic Union League. During a three-year spell at Tolka Park, Gill sampled the delights of playing in America, before moving on to Drogheda United in 1989 along with three other players from that Home Farm team. In his first season with the Louth club – along with Gerry Scully – Gill helped the side to an incredible 27-match unbeaten run and the First Division crown.
But a quick return to the second tier would follow just twelve months later, but again Gill and Scully helped the Boynesiders to a First Division title and another promotion in 1991. Once more, however, relegation was to soon follow, though Gill was to spend a part of that season on-loan at both Bray Wanderers and Sligo Rovers, then managed by Dermot Keely.
Gill earned his first job in a coaching capacity at another LSL club, Whitehall Rangers, when he decided to become Martin Kerr's assistant in ‘94 a year after the birth of his first daughter Hayley Gill. Kerr was the captain of the famous St Francis F.C. team that reached the FAI Cup final in 1990. In Gill's first season there, he, along with Warren Patmore, was sent-off in a Leinster Senior Cup match against Dundalk at Oriel Park on 18 October 1994. Three more years were to follow there and his youngest daughter Shannon Gill was born on 21 September 1996 and he took a small break from football to spend time with his family, but at the end of 1999, Gill got his first big break in his management career when he joined Billy Walsh at Kilkenny City F.C..
Bigger things were to follow, and in mid-2002, Dermot Keely asked the Dubliner to become his assistant at Kildare County, who had just joined the league. Gill accepted, but again it was a spell which was cut short, as the offer of becoming Dublin City F.C. manager was one which Gill couldn’t resist. That was despite being advised by Keely not to take the job. “Dermot said I’d never make a manager. He said I should stay with him as a coach, that I was a better coach and that I’d never be a manager because I was too nice. That kind of spurred me on a little bit.”
In his first season with the Vikings, Gill had a dream start to life as a football manager as he captured the First Division title at the first attempt. Prior to the campaign, City had been given little chance of taking the title when they were priced up at odds of 20/1, but the team were to make a mockery of that as they fought off both Bray Wanderers and Finn Harps to claim the league.
Promotion to the Premier was the resulting prize, but it was to end in disappointment for Gill as he resigned with 16 games to go. And, the boss admits that he made mistakes during that time. “We went up and we tried to do it on a very, very tight budget. I thought I could do it because I had won the First Division on a tight budget, but I soon found out that the gap was massive. I took too much on, I wasn’t a very good delegator and tried to be everything to everybody. All I was short of doing was sweeping the dressing-rooms. I tried to do everything myself, probably because I was young and naïve, and so enthusiastic.”
Roddy Collins took over at the helm but his tactics did nothing to help the club as they suffered a painful relegation. Gill counts resigning as probably his biggest regret in football, although his health and a love of the club was the reason he stood aside.
That disappointment, along with health problems, led to Gill taking a break from the game, and it wasn’t until mid-2005 that he returned to the fold when taking over as manager of Athlone Town. At the time, the midlanders were bottom of the First Division, but with the help of Gerry Scully, the pair steadied the ship, though it was not enough to help Athlone off the bottom. Gill had intended to stay with the midlands club but due to no sign of a contract renewal, he decided to take the assistant manager's job at Newry City F.C., with Dermot Keely as manager. That was a deal that soon fell through, however, as Dundalk came calling. “I had to go and tell Dermot that I was taking this job, but in fairness to Dermot, when he heard about it, he said ‘listen, you don’t even have a choice to make, it's a massive club; I’ve managed there and I’ve played there. You’ve got to take it because you don’t get opportunities like this too often.’”
Gill arrived and cleared out the deadwood before signing 13 new players. A poor pre-season had fans worried, but when Dundalk took to the field against Shamrock Rovers in the first league game of 2006, the perfect start appeared to be on the cards as the Lilywhites went in 1–0 up at the break. Disaster was to strike, however, as Rovers netted a 72nd minute equaliser before finding a dramatic injury-time winner to crush Dundalk hearts. Three poor performances and three defeats were to follow, a sequence which led to calls for Gill to leave. Four successive wins following that meant the Dubliner could breathe a little easier, but when Dundalk's inconsistency became clear as they accumulated five wins and eight losses in their first thirteen league games, the critics once again voiced their concerns, with one stating: “Gill has to leave, I’m surprised he wasn’t gone after four games”. That comment came after the home defeat to Athlone Town on 22 June…Gill’s answer to that could not have been any more emphatic, as his side went on a magnificent 20-match unbeaten run, which was eventually ended in Monaghan in the third last game of the campaign, a defeat which ultimately cost the club the First Division crown.
A 3–2 aggregate playoff win over Waterford United was not enough to earn promotion thanks to the IAG ratings, a decision which made Gill question his future in football. The boss stayed on for 2007, however, and brought Dundalk on another magnificent run as the Lilywhites went fourteen matches unbeaten at the start of the league season, a run which equalled a club record which had been set in 1987/88. Identical to that year, though, a 1–0 defeat in Cobh ended the run, and after an injury-crisis riddled Gill’s squad throughout the remainder of the season, the team went on to finish only third, having led the table up until the 22nd league game. Dundalk again entered the playoffs but lost out to Finn Harps at the semi-final stage.
He finally delivered promotion in dramatic circumstances in the last day of the 2008 season but within days his job was advertised in the local press and Gill confirmed he would not be reapplying.
In September 2009, he was appointed Assistant Manager at St Patrick's Athletic, following the appointment of Pete Mahon as Manager in place of Jeff Kenna. The club, which had finished runners-up in the League in each of the two previous seasons, had become embroiled in a relegation struggle despite having a successful UEFA Cup campaign, playing in three rounds for the second successive year. The Mahon/Gill combination steadied the ship over the remaining 9 League games, and the club finished sixth. Mahon and Gill were reappointed for the 2010 season.
In January 2014 after a spell at Malahide United F.C. Gill was appoointed assistant to Trevor Croly at Shamrock Rovers F.C. League of Ireland First Division: 2
Drogheda United – 1988–89, 1990–91
League of Ireland First Division: 2
Dublin City – 2003
Dundalk – 2008