Club Career
Bennett had a stint playing for Tiong Bahru in the Singapore Premier League as a 17 year-old in 1995, before he left Singapore to study at Loughborough University in the UK. He then returned to Singapore, and played in the S.League for Balestier Central from 1999–2000, and for Tanjong Pagar United in 2001. He won the S.League's 'Player of the Year' award at the end of the 2001 season.
Bennett then had a stint playing for Wrexham in the English football league. He helped the club win the FAW Premier Cup in 2003.
Bennett briefly returned to the S.League in 2002, playing 11 games for SAFFC during their title-winning season. He then returned to Singapore permanently in 2003 and joined SAFFC. He moved to Woodlands Wellington in 2005, before rejoining SAFFC in 2007. He was part of the SAFFC teams which won the S.League and Singapore Cup double in 2007 and 2008.
During the 2007 Singapore Cup final against Tampines Rovers, Bennett was involved in a clash with Noh Alam Shah (a Tampines Rovers striker and fellow Singapore national team player) during which 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. SAFFC ultimately won the match 4-3. The incident resulted in Alam Shah receiving a 12 month ban (reduced to 7 months on appeal).
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