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Gillespie scored his one and only Longford goal in May 2013 against Cobh Ramblers. Injuries hampered Gillespie during the 2013 season and he announced his retirement prior to the season's end. His final appearance was as a substitute during Longford's 3–1 victory at home to Finn Harps on 7 September 2013.

He was named on the League of Ireland First Division team of the season for 2012 and was also awarded Longford Town F.C. player of the year.

On 24 March 2011, Gillespie signed for League of Ireland First Division side Longford Town. Gillespie made his debut from the bench in a local derby against Athlone Town on 2 April with Gillespie's new side coming out on top by two goals to nil.

In August 2010 his ex international teammate Michael O'Neill invited Gillespie to play in a friendly for Shamrock Rovers in a reserve game versus his first club.

In October 2010, Gillespie joined up with Conference National side Darlington, later signing with the club. He made three appearances before being released on 23 December 2010.

Keith Gillespie was declared legally bankrupt on 1 October 2010 by the Belfast High Court. He estimated he lost over £7m to his gambling addiction. In 2013, he released his autobiography called How Not to Be a Football Millionaire in which he describes his gambling addiction.

Despite being recalled to Sheffield United, Gillespie failed to make another appearance and on 30 January 2009 his contract was terminated by mutual consent. He went to Bradford City with whose manager Stuart McCall; Gillespie had been a teammate at Sheffield United. However, McCall insisted Gillespie was only training with the club to stay fit and help out the younger players, and not on trial.

In 2009, Gillespie made a shock move to the east Belfast club, Glentoran. It was believed that Gillespie's agents approached Glentoran. He made his debut for Glentoran against Ballymena United in the league, he had previously played for Glentoran the night before for the reserves against Ballymena; Glentoran lost 2–1 in his 1st senior appearance for, at the time, the current league champions. In June 2010, the club announced that Gillespie was to leave after just one season after he and the club failed to agree terms on a new deal.

In July 2008, he limped out of a pre-season friendly at Bury and missed the start of the 2008–09 season. Having regained fitness he was unable to regain a first team place and was eventually loaned out to Charlton Athletic. He made only six appearances for the Addicks before being recalled to Bramall Lane as cover for mounting injuries.

Gillespie impressed McCall during training and told the manager he was very keen to gain match experience; as a result, Gillespie signed for Bradford City in March for the rest of the 2008–09 season. Gillespie was an unused substitute in their 1–0 defeat to Exeter City and so had to wait for his debut which came as a second-half substitute with City already 4–1 down to Bournemouth three days later. After just three appearances Gillespie was not offered a long-term deal by Bradford City. In the summer of 2009 he had a trial with Hungarian side Ferencváros and had been linked with a move to the IFA Premiership.

On 20 January 2007, during a Premier League match against Reading at the Madejski Stadium, Gillespie was sent off for violent conduct (elbowing Reading's Stephen Hunt) twelve seconds after coming on as a substitute. As he made his way off the pitch, Gillespie pushed Hunt in the face. He thereby achieved the dubious honour of becoming the fastest sending-off of a substitute in English football, since he was sent off before the ball had come back into play, and so technically sent off being on the pitch for zero seconds of play. The day after this incident, he stunned Sheffield United when he handed in a transfer request to the chief executive Terry Robinson but in July that year Gillespie recanted and signed a new two-year contract.

Gillespie is currently sixth place in the list of appearances for Northern Ireland with 86 caps. He made his debut in September 1994 in a 2–1 home defeat by Portugal. He played an important role in his country's 3–2 qualifying win against Spain at Windsor Park on 6 September 2006. Gillespie was investigated by the Irish FA for his involvement in a fracas with George McCartney on the trip back home from a game in Iceland in September 2007. He was not involved with the Northern Ireland set-up since being omitted from the squad that faced San Marino in February 2009. His final cap was won in a 2–0 defeat by Hungary at Windsor Park in November 2008.

Gillespie signed for Sheffield United on 5 August 2005, signing a one-year contract. This was then extended to June 2007 a month later. In his first season at the club, Gillespie played a role in Sheffield United's successful promotion campaign to the Premier League. Gillespie's most memorable goal for Sheffield United came against Charlton, where he scored the winner in the 88th minute with a stunning volley from 25 yards. This goal was also a nominee for the December Goal of the Month competition, which Paul Scholes eventually won.

Five seasons at Ewood Park brought another 138 games and 6 goals as well as another loan spell at Wigan Athletic, bringing his total appearances for Athletic to 15 from which he scored 4 goals. He then moved to Leicester City on a free transfer playing 48 games and scoring two goals in two seasons. In his time at Blackburn he started in the 2002 Football League Cup Final in which they beat Tottenham Hotspur 2–1.

In his final full season at Newcastle, the 1997–98 season, Gillespie put in arguably his best performance for the club when assisting two of Faustino Asprilla's three goals in a 3–2 Champions League victory over FC Barcelona on 17 September 1997. He also scored what he later claimed was his best goal for the club when playing up front due to an injury crisis at home to Blackburn Rovers in 1-1 draw on 25 October 1997. He also helped Newcastle to reach the FA Cup final. However, a foot injury sustained in a 0–2 defeat at Tottenham Hotspur F.C on 25 April 1998 meant, despite a fitness test, he was not in the squad for the final and Newcastle lost to Arsenal. Despite being in manager Kenny Dalglish plans, the following pre-season Gillespie failed a medical at Middlesbrough F.C but eventually departed Tyneside in a £2.3 million move to Blackburn Rovers following the appointment of Ruud Gullit as manager and a final appearance in a 2–2 draw at Middlesbrough on 6 December 1998.

He moved to Newcastle United on 10 January 1995, as a £1 million component in the £7 million deal (£6 million cash) which took Andrew Cole to Old Trafford. Gillespie had scored one of United's goals against Newcastle in the 2–0 victory at Old Trafford. This meant that he had scored twice for Manchester United in three seasons as a professional.

On 20 August 1995, the News of the World carried reports that Gillespie was subject of an approach from Alex Ferguson to return to Manchester United to fill the gap on the right wing being left by the sale of Andrei Kanchelskis to Everton, but the return to Old Trafford never happened and United instead turned to up-and-coming youngster David Beckham to occupy that position. 18 years later, Gillespie confirmed that Ferguson did contact him regarding a possible return to Manchester United, but claims that he heard nothing more about the prospective transfer after that original telephone conversation with his former manager.

Gillespie stayed at Newcastle for three-and-a-half years and during this time he played 143 games, including 15 European ties (in both the Champions League and UEFA Cup) and scored 13 goals. In both the 1995–96 and 1996–97 seasons he helped Newcastle to finish second in the Premier League (runners up to Gillespie's former club, Manchester United, on both occasions), being a key member of "The Entertainers". On the first occasion, the Magpies very nearly beat Gillespie's old club to the title, having been 10 points ahead of them by Christmas 1995 before a dismal final three months of the season saw the title sealed by Gillespie's former team mates. Initially injured from a Phil Neville tackle in a 0–2 defeat at Old Trafford on 27 December 1995 causing him to miss the following three games, at the end of the 1995–96 season Gary Lineker, then a BBC pundit, said that one of the main reasons that Newcastle lost out on the title race was because they dropped Gillespie (who had been supplying Newcastle's forwards with a stream of good crosses) for several key games in the latter part of the season.

Gillespie earned 86 caps for Northern Ireland between 1994 and 2008, putting him 6th in their most capped players of all time.

Occasional appearances for United followed in 1994–95, but he was never able to displace Andrei Kanchelskis as United's first-choice right winger.

Gillespie made his first senior appearance for Manchester United in the 1992–93 season. He scored on his debut against Bury in a 2–0 FA Cup third round triumph on 5 January 1993. He was issued with the number 31 shirt for the 1993–94 season with the introduction of squad numbers, but did not play any first team games and was loaned to Division Three club Wigan Athletic, scoring four goals in eight games.

He began his career at Manchester United after winning the FA Youth Cup in 1992, before moving to Newcastle United, where he played in the UEFA Champions League. Gillespie also played in the Premier League for Blackburn Rovers, Leicester City and Sheffield United, helping Blackburn win the Football League Cup in 2002. Towards the end of his career, he played for Glentoran in the Irish League and Longford Town in the League of Ireland.

Gillespie signed for Manchester United on leaving school in the summer of 1991, being a member of the FA Youth Cup winning side in 1992. Also in that team were Ryan Giggs, Paul Scholes, David Beckham, Gary Neville and Robbie Savage.

Keith Robert Gillespie (born 18 February 1975) is a Northern Irish retired professional footballer who played as a winger.