Bassingthwaighte made his debut in international competitions at the 2006 Commonwealth Games.[2] He finished 14th in the men's cross-country in a time of two hours, 26 minutes and 33 seconds.[2] He was over thirteen minutes behind the winner, Englishman Liam Killeen.[2] In 2007, Bassingthwaighte competed in the Namibian National Time Trial Championships.[3] He finished third, behind Jacques Celliers and Dan Craven.[3] Bassingthwaighte then competed in the 2008 Giro del Capo.[4] In the five stage race, Bassingthwaighte's best result came on the second stage,[4] held around Durbanville, where he finished 41st of 121 riders.[5] In 2009, Bassingthwaighte again competed in the Giro del Capo.[6] His best stage result was again on the second stage in Durbanville, where he finished 23rd.[6][7] Bassingthwaighte won the 2010 Namibian National Mountain Bike Championships.[8] He rode a time of one hour, 59 minutes and 29 seconds, which was eight minutes and nine seconds quicker than second-place finisher Mannie Heymans.[8] At the 2011 Namibian National Road Race Championships, Bassingthwaighte won the silver medal.[9] He finished 31 seconds behind the winner, Lotto Petrus, and two minutes and fifteen seconds ahead of the bronze medalist, Heiko Redecker.[9] In 2012, Bassingthwaighte again gained a medal in the Namibian National Road Race Championships.[10] He finished third behind Petrus and Craven.[10] Also in 2012 at the 2012 African Mountain Bike Championships Bassingthwaighte won a silver medal.[11] He finished three minutes and 44 seconds behind South African Philip Buys.[11] The bronze medalist was Rwandan Adrien Niyonshuti.[11]
2012 Summer Olympics
At the 2012 Summer Olympics in London, United Kingdom, Bassingthwaighte competed in the men's cross-country.[12] In the race on 11 August, Bassingthwaighte finished 30th, beating both Buys and Niyonshuti.[13] Bassingthwaighte's time of one hour, 37 minutes and 17 seconds was eight minutes and ten seconds slower than the time of the gold medalist, Jaroslav Kulhavý of the Czech Republic.[13]