Bainbridge did not meet with success in his early career. In 1911 he competed in the Warrnambool to Melbourne off a handicap of 30 min, finishing 65th in a time of 9h 11' 10". In 1914 he rode in the Cycle Traders 100 over finishing 87th off a handicap of 18 min.
Bainbridge returned to cycling in 1920, finishing 18th in the Goulburn to Sydney Classic. The prestigious road race of the era was the Warrnambool to Melbourne, where the fastest time carried the title of Long Distance Road Champion of Australasia. Bainbridge set the third fastest time in 1923 and the second fastest time in 1924. Bainbridge finished well back in the field in 1925 and 1926. The Warrnambool was not held in 1927 as it was replaced by the Dunlop Grand Prix, which at the time was the biggest cycling race in the British Empire and the richest race in the world. The race was held in four stages from the 14–19 November 1927, covering 690 miles. Opperman dominated the race, winning all four stages. Bainbridge finished 4th in stages 1 and 3 and 2nd in stage 4, finished third overall, behind Opperman and Watson. The Dunlop Grand Prix carried the title of Long Distance Road Champion of Australasia. One consequence of the Dunlop Grand Prix was the public subscription, organised by the Sporting Globe to send Opperman and an Australian team to the Tour de France. Writing after the Dunlop Grand Prix, Opperman paid tribute to 3 riders, Watson, Bainbridge and Osborn and these were the riders selected to travel with him to France. Bainbridge was captain of the Preston Cycling Club.
1928 Tour de France
In 1928, aged 37, Bainbridge set sail for the Tour de France. The shortest day was 119 km and the longest 387 km. There were plans to bolster the 4 Australasians with European riders however these did not come to fruition, with the result that the 4 Australasian riders were up against teams of up to 10 riders. Their position was worsened by Henri Desgrange's plan to run most of the race as a team time trial, as he had the previous year. Teams started at intervals and shared the pace until the end. Desgrange wanted to stop riders racing casually for all but the last hour. The American historian Bill McGann wrote: With four rather than 10 riders to share the pace, Opperman and his team were handicapped. The Franco-American writer René de Latour wrote: Opperman said of the long stages and the hours of darkness that riders endured: Bainbridge had his highest finish in stage 8 where he finished 20th. He was forced to withdraw in the fifteenth stage in the French Alps due to saddle sores and infected wounds from crashes.
