Early career and club debut Bennett was selected to join the FAS Milo Scheme for talented young footballers at the age of 12.
Balestier Central Bennett returned to Singapore in 1999 hoping to make a career as a professional footballer. Then
Balestier Central coach P. N. Sivaji gave him his first opportunity with the
S.League club.
Tanjong Pagar United Bennett moved to previous club
Tanjong Pagar United (formerly Tiong Bahru) in May 2000. Having played as a
midfielder for 15 years, his defining career shift to defence came when coach Tohari Paijan played him as a
centre-back in the absence of regular stopper
Lim Tong Hai in a league match. Recognition of his performances came when he was selected in the Singapore selection that faced
Manchester United and
Liverpool in a couple of high-profile friendly matches, and culminated in a S.League Player of the Year award.
Wrexham Bradford City manager
Jim Jefferies was impressed with Bennett and offered him a trial at the Yorkshire club. On 8 February 2002,
Wrexham manager
Denis Smith signed him on a short-term contract til the end of the
2001-02 Football League. Although it is not known how much Wrexham had paid to secure the deal, the club's fans paid money to ensure the club could secure Bennett's signature. He made his league debut against
Port Vale on 6 March 2002, partnering
Trinidad & Tobago international
Dennis Lawrence in the heart of defence. He was assessed as "enjoying a remarkable start, looking composed at the back and reading the game superbly" by the fans, who had contributed money to sign the player. Bennett made over 20 appearances for the Welsh side but with the Welsh side 4th from bottom in the league, relegation was confirmed at the end of the season. He returned to Wrexham in the
2002-03 season. Bennett was offered new terms by Wrexham at the end of the season but chose to reject the contract to return to Singapore to improve his chances of featuring regularly for the national team.
Return to the S.League Amid interest from
Home United,
Tampines Rovers and
Woodlands Wellington after his Wales stint, Bennett signed for defending champions Singapore Armed Forces in mid-2003.
Woodlands Wellington He moved to ambitious
Woodlands Wellington in 2005, joining his international colleagues
Agu Casmir,
Itimi Dickson,
Goh Tat Chuan and
Masrezwan Masturi. Bennett led the team to 3rd place in the
2005 S.League, and 2nd and 3rd placing in the 2005 and 2006
Singapore Cup respectively.
Back to SAFFC After two seasons with the Rams, Bennett rejoined Singapore Armed Forces for a second time, achieving the S.League and Singapore Cup double in 2007 and 2008. In the 2007 Singapore Cup final won by Singapore Armed Forces on 25 November, Bennett was involved in a clash with
Tampines Rovers'
Noh Alam Shah, a fellow Singapore national team player towards the end of the match. Noh Alam Shah kneed Bennett in the head in a tussle for the ball and after being dragged away by his team-mates, returned and kicked Bennett in the head. Bennett was knocked unconscious and had to be taken to hospital while Alam Shah was sent off by referee Abas Daud. The incident resulted in Alam Shah receiving a 12-month global ban which was reduced to 7 months on appeal. Bennett was handed the club's captaincy in 2012. As captain he won the Singapore Cup in 2012 as well as the league title in 2014.
Geylang International After playing for the
Warriors for nine years and amassing four league titles and winning the
Singapore Cup three times, Bennett signed for
Geylang International ahead of the
2016 S.League campaign. He was a key cog of the Eagles defence, helping the team to the league's third-best defensive record, with 29 goals conceded in 24 games as Geylang finished fifth in the nine-team competition.
Tampines Rovers In 2017, Bennett joined the 6th S.League club of his career, signing for
Tampines Rovers for the
2017 S.League season. On 7 July 2021, Bennett scored the only goal for Tampines Rovers in the
2021 AFC Champions League group stage fixtures encounter against
Gamba Osaka in an 8–1 defeat at the
Bunyodkor Stadium in
Tashkent, Uzbekistan. At 43 years and 181 days, Bennett also eclipsed
Dejan Damjanović (39 years and 341 days) as the oldest ever scorer in the tournament's history.
Tanjong Pagar United In January 2022, Bennett returned to
Tanjong Pagar United for the second time after over 20 years. He will play for the Jaguars for the
2022 Singapore Premier League season. On 9 March 2022, Bennett scored a header against
Hougang United which put him to become the league's oldest scorer at 44 years and 239 days, breaking
Aleksandar Đurić's record of scoring at 43 years and 284 days. ==International career==