He came through the youth structures at Wellington-based side Boland Cavaliers and played for the Boland U21 side in 2007 and 2008.
He graduated to the senior side in 2009, being named in the 2009 Vodacom Cup squad.[2] He made his debut in the first round of this competition, starting in an 18–43 loss to the Sharks XV.[3] He started all six of Boland's matches in that competition and was also included in their Currie Cup squad for the 2009 Currie Cup Premier Division competition.[4] He made his Currie Cup debut by starting in the first match of the season, a 26–18 victory over the Leopards.[5] He made 11 appearances in total, as well as the second leg of their promotion/relegation series against the Pumas,[6] a result that saw Boland relegated to the 2010 Currie Cup First Division.
Bester remained in the Premier Division however, by joining the Pumas for the 2010 season. He didn't feature in the 2010 Vodacom Cup, but he did make his Pumas debut in their opening 2010 Currie Cup Premier Division match against the Blue Bulls.[7] He made seven appearances in total for the Pumas, scoring one try.
He remained with the Pumas for just one season before returning to former side Boland Cavaliers. He remained a regular in the team during his three-year spell there, making close to fifty appearances in the Vodacom Cup and Currie Cup competitions.
He left Boland for the second time after the conclusion of the 2013 Currie Cup First Division season though, joining near-rivals SWD Eagles prior to the 2014 season.[8]