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| Cromwell Cup | | | | | | | |
| Year | Winner | Age | Sire | Driver | Trainer | Distance | Time |
| 2008 | Waihemo Cullen | 4 yr old gelding | Christian Cullen | NP Williamson | AW Faulks | 2600 metres | 3-23.0 |
| 2009 | Luckisaladytonight | 6 yr old mare | Presidential Ball | JR Dunn | RJ Dunn | 2600 metres | 3-23.5 |
| 2010 | Niraadi | 6 yr old gelding | Sir Vancelot | DJ Dunn | RJ Dunn | 2600 metres | 3-25.0 |
| 2011 | Beaudiene Christian | 4 yr old entire | Christian Cullen | NR McGrath | NR McGrath | 2600 metres | 3-25.4 |
| 2012 | Glencoe V C | 4 yr old gelding | Washington V C | BD McLellan | BD McLellan | 2600 metres | 3-20.8 |
| 2013 | Smiling Star | 4 yr old gelding | Grinfromeartoear | RD Holmes | RD Holmes | 2600 metres | 3-28.9 |
| 2014 | Devil May Care | 5 yr old gelding | Falcon Seelster | RT McIIwrick | AFH Hunter | 2600 metres | 3-37.4 |
| 2015 | Cyclone Kiwi | 4 yr old gelding | Jereme's Jet | RD Holmes | RD Holmes | 2600 metres | 3-20.9 |
| 2016 | Clive | 4 yr old gelding | Gotta Go Cullen | Chris Thornley | Don Ross | 2600 metres | 3-25.9 |
| 2017 | Glenferrie Classic | 4 yr old mare | Bettor's Delight | Sam Ottley | Mark Jones | 2600 metres | 3-27.2 |
| 2018 | Four Starzz Shiraz | 7 year old gelding | Four Starzzz Shark | Charlotte Purvis | Brad Mowbray | 2600 metres | 3-22.2 |
| 2019 | Zadaka | 6 year old gelding | Mach Three | John Dunn | Robert Dunn | 2600 metres | 3-42.6 |
| 2020 | I'mallaboutthebase | 5 year old mare | Shadow Play | Sam Ottley | Steve Baucke | 2600 metres | 3-27.2 |
| 2021 | Plutonium Lady | 4 year old mare | Bettor's Delight | Blair Orange | Mark Jones | 2600 metres | 3-28.4 |
| 2022 | Macandrew Aviator | 5 yr old gelding | Panspacificflight | Craig Ferguson | Kirstin Barclay | 2600 metres | 3-31.6 |
