Robert Jolly joined the East Liverpool Wheelers in 1906, and that year won both the club and Liverpool District unpaced 50 miles time-trials. He also finished runner-up to Tom Sherratt of Wigan in the NCU Liverpool Centre 50-mile Championship. In 1907, however, Jolly won the Liverpool Centre 50-mile title and also the tandem title with fellow Wheelers rider J. Norman, with whom he would also compete at the Olympics a year later. Jolly moved to Sefton Harriers for the 1908 season, and failed to retain his 50-mile title when runner-up to Wigan’s Ben Jones. He won a second Liverpool Centre tandem title in 1909, this time with F. Kinghorn.