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On 6 February 2015, Bennett returned to his home-town club, Cork City He scored City's first goal in European Competition since 2007 in their opening game against KR Reykjavik on 2 July 2015. On his return he has won the 2016 Presidents Cup and the FAI Cup both against Dundalk On 5 November 2017, Cork City captained by Bennett completed the league and cup double after defeating Dundalk in the 2017 FAI Cup Final.

Following his contract termination, he signed for fellow League Two team AFC Wimbledon also on 31 January 2013. The ability and experience Bennett brought to the AFC Wimbledon defence in the second half of the 2012–13 season helped "The Dons" avoid relegation from the Football League and remain a League Two team for a third successive season.

Bennett received a call up for the Republic of Ireland under–21 team in 2001. In 2007 Bennett was called up to the Ireland 'B' squad for a game against Scotland 'B' in Airdrie.

On 4 July 2011 Bennett joined Cheltenham Town on a one-year contract. Bennett was made captain of Cheltenham by manager Mark Yates shortly after his arrival. Bennett formed an excellent defensive partnership with Steve Elliott that saw Cheltenham spend much of the season chasing automatic promotion. Bennett played a big part in Cheltenham reaching the 3rd round of the FA Cup which drew them away to Tottenham Hostspur. They went on to lose 3–0; however, the game will go down as one of the biggest days in the club's history. Cheltenham's form suffered after the FA Cup game but they still managed to seal a League Two play-off position under Bennett's captaincy. Cheltenham went on to beat Torquay United in the play-off semi-finals, but lose the play-off final to Crewe Alexandra, thus confirming another season in League Two. On 31 January 2013, Bennett left Cheltenham after his contract was terminated by mutual consent.

On 16 February 2010 Bennett joined Wycombe Wanderers on a one-month emergency loan. He returned to Brentford at the end of the loan period because of the Bees' lack of defensive cover, but signed a new loan deal with Wycombe until the end of the season on 25 March 2010. One week later, before he had made any further appearances for the club, he sustained an ankle injury that looked to have ruled him out for the rest of the season and he returned to Brentford for treatment. However, he recovered quicker than expected and returned to training at Wycombe in late April. He returned to the team for the final game of the season against Gillingham, scoring his first goal for the club during this match.

On 23 July 2010 Bennett joined Wycombe Wanderers on a permanent one-year contract. Bennett was part of the Wycombe squad that achieved automatic promotion to League One that year, unfortunately injuries limited his appearances.

He signed a permanent contract with Brentford on 30 July 2009 which was set to run until June 2011 and was appointed club captain.

On 28 July 2008, Bennett was told that he did not feature in Reading's plans and was told to find a new club. He began a second loan spell at Brentford on 8 August 2008, initially for one month, although this was extended to five months on 31 August 2008, following Man-of-the-Match performances against Rotherham United and Notts County. His loan was then extended for a third time until the end of the 2008–09 season. Bennett appeared in over 50 games for Brentford in the 2008–09 season and assumed the role of team captain in the absence of regular captain Kevin O'Connor. As O'Connor was out for the match that decided if they won the league or not Bennett was made captain and lifted the League Two trophy after a 3–1 victory over Darlington. Bennett scored the opening goal in this fixture. At the end of the 2008–09 season, Bennett was released by Reading.

Following several bids, Bennett joined Reading on a two and a half-year contract for an undisclosed fee thought to be £250,000 on 30 January 2007.

On 31 July 2007, he was loaned for six months to Southampton and made his debut during a home defeat to Crystal Palace. He returned to Reading in January 2008. On 7 March 2008, he joined Brentford on loan during this time Bennett scored his first goal in English football against Bradford City.

In May 2007, he was called up to the full Republic of Ireland team for their two match trip to the United States. Bennett played the full 90 minutes against Ecuador, helping Ireland to a 1–1 draw. He then played in the following match against Bolivia, which also ended 1–1, during which he made a saving tackle to keep the Bolivian team from going ahead.

Alan John Bennett (born 4 October 1981) is an Irish professional footballer who plays for Cork City as a defender. He has represented the Republic of Ireland national team.

Bennett was born in Cork, Republic of Ireland on 4 October 1981. He began his footballing career at his local club Richmond, based in Waterfall, County Cork, which competes in the West Cork League. He was coached by highly regarded coach Colm Donovan. Bennett subsequently joined League of Ireland Premier Division club Cork City in 2000 at the age of 18. He initially played as a midfielder, but was converted to the defensive role of centre-back during the 2004 season. He made more than 150 appearances for the "Rebel Army", scoring ten goals. During his time at Cork City, Bennett played in The UEFA Cup and Champions league and also won a FAI Youth Cup medal in 2000, National league Medal in 2005 and 3 Munster Senior Cup medals.