Cooper’s Hill Cheese Rolling records: the winners, legends and repeat champions to know

The easiest way to fall down a Cooper’s Hill rabbit hole is through the names. Our Cooper’s Hill Cheese Rolling winners archive now pulls the recorded winners into one updateable table, covering every available category from the historic downhill races to the modern uphill contests.

That archive is useful because the event is not just one chaotic sprint. Over the years it has included several men’s downhill races, a women’s downhill race, children’s uphill races and an adult mixed uphill race. Some records are neat. Others are delightfully messy.

The repeat winners

Cooper’s Hill has always rewarded a particular blend of balance, bravery and an apparently relaxed attitude to bruises. Some competitors have won again and again, turning a one-off Gloucestershire spectacle into a personal tradition.

• Chris Anderson is one of the modern names most closely associated with the event, with a long run of men’s downhill wins and wide coverage when he broke records.
• Flo Early became one of the standout women’s champions, with multiple wins in the women’s downhill race.
• Leilani Ryder is prominent in the children’s uphill records, showing that the uphill contests have their own repeat names too.
• Older records include names such as Izzy John, Steven Brain and Stephen Gyde, though historic entries can carry caveats where source records are incomplete or marked unconfirmed.

The international pull

Although it is rooted in Brockworth and Gloucestershire, the event has become a global curiosity. Recent winners and competitors have come from well beyond the county, including Germany, Japan, Canada, the United States, New Zealand and other countries. It is local folklore with an international guest list.

Why the records need caveats

Cheese Rolling is older than its tidy online paperwork. Some years were cancelled, some races changed category, some old results are incomplete, and a few entries are marked unknown or unconfirmed. That is why the winners archive keeps the notes column visible rather than sanding off the interesting edges.

What to watch in 2026

The next update will be straightforward: after the 2026 event, the new winners can be added to the table, with the source note updated at the same time. The fun bit will be seeing whether the day produces a new first-time winner, another repeat champion, or a fresh name for the records.

For the full year-by-year list, including all available categories and source notes, go to the Cooper’s Hill Cheese Rolling winners archive.

Sources and further reading: Cheltenham Times winners archive BBC 2025 cheese rolling guide Guinness World Records: most wins of a cheese-rolling race