The Chester Cup is a flat handicap race for horses aged 4 and above. The race is run over a distance of 2 mile 2 furlongs and 147 yards at the Chester May meeting.
For the best odds on the Chester Cup check out the prices available via the betting exchanges at Betfair, Betdaq and the World Betting eXchange.
If you take an early bird price on the morning of the Chester Cup and the SP is greater bet365 will pay out at the bigger price.
| 2009 : Totesport.com Chester Cup Heritage Handicap |
| Going : Good to Firm, Good in places | 16 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Daraahem | B W Hills | R Hills | 7/1 |
| 2 | Ajaan | H R A Cecil | T P Queally | 11/1 |
| 3 | Halla San | R A Fahey | P Hanagan | 20/1 |
| 4 | Desert Sea | D W P Arbuthnot | Martin Dwyer | 14/1 |
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| 2008 : Totesport.com Chester Cup Heritage Handicap |
| Going : Good | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Bulwark | Ian Williams | Jim Crowley | 33/1 |
| 2 | Som Tala | M R Channon | L Dettori | 10/1 |
| 3 | Tilt | B Ellison | J Murtagh | 8/1 |
| 4 | Double Banded | J L Dunlop | K McEvoy | 9/2 |
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| 2007 : Totesport Chester Cup Heritage Handicap |
| Going : Good to Firm, Good in places | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Greenwich Meantime | R A Fahey | P Hanagan | 14/1 |
| 2 | Fair Along | P J Hobbs | J P Spencer | 11/2 |
| 3 | Enjoy The Moment | J A Osborne | Martin Dwyer | 14/1 |
| 4 | Under The Rainbow | B W Hills | J Fortune | 25/1 |
| |
| 2006 : Totesport Chester Cup (heritage Handicap) |
| Going : Good to Firm | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Admiral | T J Pitt | J F Egan | 28/1 |
| 2 | Vinando | C R Egerton | L Dettori | 7/1 |
| 3 | Greenwich Meantime | R A Fahey | P Hanagan | 11/2 |
| 4 | Dancing Bay | N J Henderson | J P Spencer | 20/1 |
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| 2005 : Totesport Chester Cup Handicap |
| Going : Good to Soft | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Anak Pekan | M A Jarvis | P Robinson | 16/1 |
| 2 | Swift Sailor | M Johnston | K Darley | 13/2 |
| 3 | Contact Dancer | M Johnston | R Ffrench | 16/1 |
| 4 | Larkwing | G Wragg | R Mullen | 15/2 |
| |
| 2004 : Totesport Chester Cup (Heritage Handicap) (Class B) |
| Going : Good | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Anak Pekan | M A Jarvis | P Robinson | 2/1 |
| 2 | Misternando | M R Channon | S Hitchcott | 33/1 |
| 3 | Big Moment | Mrs A Perrett | D Holland | 7/1 |
| 4 | Distant Prospect | A M Balding | Martin Dwyer | 15/2 |
| |
| 2003 : Tote Chester Cup (Showcase Handicap) |
| Going : Good to Firm | 16 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Hugs Dancer | J Given | Dean McKeown | 9/1 |
| 2 | Big Moment | Mrs A Perrett | D Holland | 9/2 |
| 3 | Knavesmire Omen | M Johnston | J Fanning | 16/1 |
| 4 | Rahwaan | C W Fairhurst | F Norton | 50/1 |
| |
| 2002 : Tote Chester Cup (Showcase Handicap) (Class B) |
| Going : Good to Firm, Firm in places | 18 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Fantasy Hill | J L Dunlop | Pat Eddery | 8/1 |
| 2 | Rainbow High | B W Hills | R Hughes | 6/1 |
| 3 | High And Mighty | G Barnett | F Norton | 12/1 |
| 4 | Riyadh | M Pipe | J Mackay | 16/1 |
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| 2001 : Tote Chester Cup (Showcase Handicap) |
| Going : Good to Firm, Firm in places | 17 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Rainbow High | B W Hills | R Hughes | 9/2 |
| 2 | High And Mighty | G Barnett | J McAuley | 33/1 |
| 3 | Prairie Falcon | B W Hills | Dale Gibson | 12/1 |
| 4 | Cover Up | Sir Michael Stoute | F Lynch | 12/1 |
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| 2000 : Tote Chester Cup (Showcase Handicap) |
| Going : Good, Good to Firm in places | 18 ran |
| Pos | Horse | Trainer | Jockey | SP |
| 1 | Bangalore | Mrs A Perrett | G Bardwell | 16/1 |
| 2 | Ansar | D K Weld | F Norton | 11/1 |
| 3 | Fantasy Hill | J L Dunlop | G Carter | 15/2 |
| 4 | Prairie Falcon | B W Hills | J Mackay | 8/1 |
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