The school has a long history of sport and St Mary's College Mead, at the centre of the school buildings, was first used for bicycle races on September 1st 1881, with an event organised by the Winchester & County Cycle Club. W Snook from Winchester and his brother, from Southampton BC, took the lion's share of the prizes.
Winchester & CCC held their second annual race meeting at the College Meads on August 23rd 1882. The program was a 1 and 3 miles open handicap races, 1 mile open tricycle handicap race, ¼ mile handicap foot race, 3 miles handicap race for club members and a 1 mile race for club members who had never won a prize.
The sports were repeated the following year on August 27th 1883. The market out grass course was described as bumpy in places, with the corners rounded off "somewhat unnecessarily sharp", which explains the spills at the meeting. W Snook, the captain of Winchester CC and his two brothers again did well at the meeting.
The College Mead was used for bicycle races several times over the next twenty years. These meetings included the Oddfellows' fete in 1886, a Cyclists' Tournament on August 16th 1892 with twelve events, including seven bicycle races and St Thomas' Young Men's Club sports in 1894. The last bicycle race at College Mead was organised by Winchester Cycle Club and was held on August Bank Holiday 1905.
The College Mead at Winchester College remains as it has been for centuries and is used for cricket.
Other locations in Winchester that organised bicycle races, include Bar End cricket ground where a Coronation sports meeting in Winchester was held on June 26th 1902 and included a club race for Winchester Cycle Club. The Roebuck ground was also used in 1908 for sports meetings at which Winchester Cycle Club organised races.