The Highlander Stakes is a Canadian Thoroughbred horse race run annually at Woodbine Racetrack in Toronto, Ontario. Run in mid to late June, the Grade II race is open to horses aged three and older. Raced over a distance of six furlongs on turf, it currently offers a purse of $200,000. Inaugurated in 1954 as the Highlander Handicap at Toronto's Greenwood Raceway, it was moved to Woodbine Racetrack in 1957. The race was contested on dirt through 2003 when it was moved to the turf for the 2004 edition. It has been run at a distance of six furlongs except for 1957 and 1958 when it was set at seven furlongs. The race was upgraded to Grade II status in 2010.
| Stakes Race | Grade | Purse |
|---|---|---|
| Eclipse Stakes | III | $150,000 |
| Nassau Stakes | II | $300,000 |
| King Edward Stakes | II | $250,000 |
| Highlander Stakes | II | $200,000 |
| Singspiel Stakes | III | $150,000 |
| Queen's Plate Stakes | I | $1,000,000 |
| Dominion Day Stakes | III | $200,000 |
| Dance Smartly Stakes | II | $300,000 |
| Ontario Matron Stakes | III | $150,000 |
| Nijinsky Stakes | II | $300,000 |
| Royal North Stakes | III | $150,000 |
| Sky Classic Stakes | II | $250,000 |
| Ontario Colleen Stakes | III | $150,000 |
| Play the King Stakes | II | $200,000 |
| Seaway Stakes | III | $150,000 |
| Natalma Stakes | III | $200,000 |
| Summer Stakes | III | $250,000 |
| Canadian Stakes | II | $300,000 |
| Northern Dancer Turf Stakes | I | $500,000 |
| Woodbine Mile Stakes | I | $1,000,000 |
| Selene Stakes | III | $250,000 |
| Grey Stakes | III | $200,000 |
| Nearctic Stakes | I | $500,000 |
| E.P. Taylor Stakes | I | $1,000,000 |
| Canadian International Stakes | I | $1,500,000 |
| Autumn Stakes | II | $150,000 |
| Kennedy Road Stakes | III | $150,000 |
| Bessarabian Stakes | III | $150,000 |
| Valedictory Stakes | III | $150,000 |
