Charlton Athletic McGleish was born in
Barnet,
Greater London. At the age of 20, McGleish was loaned to Leyton Orient for the first of four spells at the club. During this loan, he made six appearances and scored his first senior goal in league football. He returned to Charlton but made only a limited number of starts. He then moved to Peterborough United, where he made only a few substitute appearances. He was sent out on loans to
Colchester United and
Cambridge United.
1997–2007 He was subsequently sold to his previous club,
Leyton Orient, now holding a constant place in the team, and in his one-year spell back at Brisbane Road he scored seven goals. After this single season he was sold to
Barnet, where he stayed for four years and had a goals-to-game ratio of a goal every 3.6 games. He then returned to Colchester United, where he averaged a similar goal-scoring tally. He moved to
Northampton Town in 2004 under a
Bosman transfer and was their player of the year in his first season. In 2006, he retained the player of the season accolade, Northampton's first player for 31 years to do so. McGleish was loaned out to his former club
Northampton Town on 28 October 2008 for a month's loan lasting until 25 November, wearing shirt number 27. He scored his first goal in his second spell in a first-round
FA Cup tie at
Elland Road against
Leeds United on 7 November. On 10 May 2011, McGleish was released by Leyton Orient after his fourth stint with the club, despite being the club's top scorer of the
2010–11 season with 17 league goals. McGleish revealed that he had not been offered a new contract and added that he was "gutted and a little bit shocked", although he had suspected that he would be released.
Bristol Rovers On 29 June 2011, he signed a contract with recently relegated
Bristol Rovers. McGleish stated that his desire to work with manager
Paul Buckle was the main reason for him signing. On 6 August 2011, the opening day of the 2011–12 season, McGleish scored Rovers' first goal and set up another on his debut for the club in their 3–2 win at
AFC Wimbledon. McGleish re-joined
Barnet on a short-term loan deal on 1 March 2012. On 17 May 2012, McGleish was released by the Rovers. In November 2012, McGleish joined
Chesham United on a free transfer from
Whitehawk. In October 2018, McGleish departed the club alongside fellow coaches Mark Swales and Dave Sandiford. He returned to
Hendon as a player-coach in December 2018, a club he played for as a youth in the early 90s.
Leverstock Green In June 2021, McGleish joined
Leverstock Green as player/assistant manager, joining new manager Fergus Moore. He made 20 league appearances in his first season with the club and 20 in all competitions in
the following season, but saw his playing time drastically reduced in the
2023–24 season, in which he made only three league appearances and five in all competitions. In the second of these, a 0–0 draw with
Cockfosters on 23 March 2024, he achieved the distinction of having played beyond the age of 50; however, the
2024–25 season brought only a further three appearances in the league, the last of these coming in October 2024 in a 3–3 draw with
Biggleswade. In August 2025, after ten months away, he made his return to the first team in a 3–2 victory at
Stotfold, coming on as an 89th-minute substitute. == Managerial career ==