Vuelta a Burgos
Bennett started his 2020 season at the Tour Down Under where he placed 8th overall. In February at the National Championships, Bennett finished second in the road race after spending out in front by himself only for Shane Archbold to catch and sprint past him on the line. When the season resumed after the interruption by the COVID-19 pandemic, he managed to get 5th overall in both the Vuelta a Burgos and the Tour de l'Ain. He participated in the Tour de France, where he wore Māori-themed Shimano S-Phyre shoes painted by his artist girlfriend, Caitlin Fielder.