It began play in 1901 under the Ontario Football Association League, now known as the Ontario Soccer Association, and is the oldest soccer competition in North America.

The cup was first played as a senior men's tournament in 1901, making it one of the oldest active sporting competitions in Canada.

[1] It has been held every year since, with the exception of the World Wars.

The competition is played from May to September every year to crown a champion in each of 22 divisions, including different age levels for boys, girls and adults, and a Special Olympics division.

[2] The Ontario Cup winners from the under-14, under-16, under-18 and senior open divisions advance to the Canadian National Challenge Cup to compete against the cup winners from other provinces in Canada.