Bicycle racing at the show's athletic sports were held on a grass track and the 1898 sports included half, one and two miles bicycle handicap races. By the 1899 show, newspaper reports mention "Cycle gymkhana in the afternoon and athletic sports in the evening."
The Sheffield Daily Telegraph of July 21st 1904 reported that five men from Hull appeared before the Scunthorpe police court charged with betting at the Winterton Show Sports. "They received and paid out money on the cycle and foot races." Their defence was that betting was allowed at other Lincolnshire sports meetings, but they were fined £1 each.
At the Show sports on June 29th 1906 the events were; half, one and two miles bicycle handicap races, 100, 200 yards, half and one mile running races and a walking race. The Barton Cycle Works brass band played at the sports and there was a firework display in the evening. Minnie Sylvester was fine one shilling for riding home to Scunthorpe after the show without lights on her bicycle.
Bicycle racing at Winterton Show was advertised as being under NCU rules from the 1910's. By 1920, bicycle races at the sports event consisted of a mixture of half and one mile scratch and handicap races and there were 415 entries with 3,000 spectators. In 1926 there was a "Pitmen's Cycle Derby" one mile handicap race. There was a record 10,000 crowd at the 1937 sports and the sons of national championship riders ‘Lal' and Charlie White rode successfully.
The sports continued in the run up to the Second World War and resumed after the war and into the 1950's. Attendance at the show was still very high, with 10,000 attending in 1953 to see the only cycle event a 1,000 yards handicap race. Bicycle racing at Winterton Show continued until at least 1958. The show is still very popular.