The history of the Diamond Mile, which at the start was the richest race in the English-speaking Caribbean) features a very exclusive list of elite thoroughbreds currently existing at Caymanas Park.
The event took a hiatus after 2019 when the December marquee slot was reinvented as the Mouttet Mile, but it has made its highly anticipated return to the racing calendar.
The renewed Diamond Mile will be contested on Saturday, July 26, 2026.
The past winners of the Jamaica Diamond Mile include:
Past Winners Table
| Year | Winner | Jockey | Trainer |
| 2019 | She's A Maneater | Omar Walker | Wayne DaCosta |
| 2018 | Will In Charge | Robert Halledeen | Robert Pearson |
| 2017 | She's A Maneater | Dane Nelson | Wayne DaCosta |
| 2016 | Seeking My Dream | Omar Walker | Wayne DaCosta |
| 2015 | Seeking My Dream | Omar Walker | Wayne DaCosta |
Notable Historic Facts:
The DaCosta Dominance: Legendary late trainer Wayne DaCosta won four out of the first five stagings of the race (twice with Seeking My Dream and twice with the brilliant She's A Maneater).
The First 'Diamond': Seeking My Dream carved his name into history by winning the inaugural running in 2015 and successfully defending his title in 2016.
Drama in 2018: Will In Charge took the 2018 crown in a thrilling, incident-packed race after the heavy favourite She's A Maneater bolted from the gates before the start and was declared a late non-starter.
