The Highlander Stakes is a Thoroughbred horse race run annually at Woodbine Racetrack in Toronto, Ontario, Canada. 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 $250,000.

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 run at seven furlongs.

The race was upgraded to Grade II status for 2010, fell to a Grade III, and restored as a Grade II event in 2014.^[1] In 2018, the Jockey Club of Canada moved it to Grade I status.^[2]

The event was downgraded to Grade II in 2022.^[1]

Speed record: (through 1998, times were recorded in fifths of a second. Since 1999 they are in hundredths of a second)

• 1:07.13 - Long On Value (2018)

Most wins:

• 2 - Signature Red (2010, 2011)
• 2 - Stutz Bearcat (1979, 1980)
• 2 - Wake At Noon (2000, 2002)
• 2 - Soaring Free (2004, 2005)
• 2 - Smart Enough (2007, 2009)

Most wins by an owner:

• 6 - Sam-Son Farm (1973, 1978, 1979, 1980, 2004, 2005)

Most wins by a jockey:

• 4 - Todd Kabel (1997, 2003, 2004, 2005)

Most wins by a trainer:

• 4 - Lou Cavalaris, Jr. (1959, 1964, 1969, 1977)

• List of Canadian flat horse races