Mainly a centre-back, Bennett is a versatile player who is a strong reader of the game, allowing him to make crucial interceptions despite not being blessed with great pace; he is also known for his trademark long-range free kicks.

He was educated in Singapore at Tanglin Trust School and the United World College of South East Asia, where his father Andrew was a teacher and later headmaster until 2004.

[4] He was drafted as a trainee by National Football League side Tiong Bahru three years later, giving him the opportunity to train with the team before he left Singapore to further his tertiary studies in England.

[13] 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.

[17][18] 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.

[19] 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.

[20] He moved to ambitious Woodlands Wellington in 2005, joining his international colleagues Agu Casmir, Itimi Dickson, Goh Tat Chuan and Masrezwan Masturi.

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.

[28] 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.

[29] He made 31 appearances in all competitions for the Stags last season and was a key member of league's best local defence, earning him a two-year extension with the club despite almost reaching 40 years old.

[30] 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.

[37][38][nb 2] With his 122nd appearance in the away leg of the 2012 ASEAN Football Championship finals, Bennett surpassed Aide Iskandar and Malek Awab as Singapore's most capped player.