The Durham Cup Stakes is a Thoroughbred horse race run annually at Woodbine Racetrack in Toronto, Ontario, Canada. Run in mid October, the Grade III race is open to horses age three and older. Raced over a distance of 1+1⁄8 miles on Tapeta synthetic dirt, it currently offers a current purse of Can$150,000.

The race was first run in 1906 as the Durham Cup Handicap at Old Woodbine Racetrack. It remained there until the track was closed and replaced by the new Woodbine racetrack. Since inception it has been contested at various distances:

• 1+3⁄4 miles : 1906-1951
• 1+1⁄4 miles : 1952-1979
• 1+1⁄8 miles : 1980–2019
• 1 ¹⁄₁₆

In 1992, Francine Villeneuve became the first female jockey to win the race.

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

• On Synthetic dirt surface:
  • 1:40.73 - Who's the Star (2022)
• On natural dirt:
  • 1:48.58 - Deputy Inxs (1999)

Most wins:

• 3 - Basqueian (1994, 1995, 1996)

Most wins by an owner:

• 4 - Joseph E. Seagram (1906, 1908, 1909, 1910)
• 4 - Seagram Stable (1926, 1928, 1929, 1932)
• 4 - Windfields Farm (1962, 1966, 1971, 1973)

Most wins by a jockey:

• 5 - Emma-Jayne Wilson (2006, 2011, 2015, 2022, 2023)

Most wins by a trainer:

• 6 - Roger Attfield (1987, 1989, 1990, 2001, 2008, 2016)

• List of Canadian flat horse races