The Chester Racecourse's May Festival, staged generally early in the month, has been an annual fixture at this historic racecourse since 1766. It features about 20 individual races ranging from Maiden events to highly prestigious Class 1&2 events, which range from £11,000 to £120,000 in prize money.
Day One - Totesport Cup Day - features not only the feature race of the Totesport Cup but also the much anticipated Cheshire Oaks, a Listed race which is seen as the unofficial trial to the Epsom Oaks. Further races on the first day of the festival include the Manor House Stables Lily Agnes Stakes and the Clatterbridge Cancer Research Handicap Stakes; two five furlong sprint races that will leave you breathless.
Day Two - the infamous Boodles Ladies' Day - is dedicated to the best Group 3 races the county has to offer. It features the Huxley Stakes and the Chester Vase, both valuable races often entered by future starters in the Epsom Derby. It also includes a best dressed competition for the ladies on the course. It is the most glamorous day of the Chester racing season.
Day Three - Boodles City Day - wraps up the three days of racing action with a number of great quality Group3 races. The third day of the May Festival at Chester features the Ormonde Stakes, a one mile and five furlong race for an impressive purse of £75,000; as well as the Goddard Dee Stakes run over one mile and two furlongs.
The Chester Cup, currently referred to as the Totesport Cup after its sponsor, was inaugurated in 1824. The race is open to thoroughbreds aged four and older and is run over the gruelling distance of two miles, two furlongs and 147 yards - a distance that was introduced in 1994.
The Chester Cup has been an annual event for almost 200 years and has rarely been cancelled in its long history. The most recent abandonment of this well-loved race was in 1983, when the track was flooded and subsequently waterlogged.
| Year | Winner | Jockey | Trainer | Time |
| 2009 | Daraahem | Richard Hills |
Barry Hills |
4:04.01 |
| 2008 | Bulwark | Jim Crowley |
Ian Williams |
4:06.57 |
| 2007 | Greenwich Meantime | Paul Hanagan |
Richard Fahey |
3:58.89 |
| 2006 | Admiral | John Egan |
Tim Pitt |
4:03.34 |
| 2005 | Anak Pekan | Philip Robinson |
Michael Jarvis |
4:14.60 |
