[2] The current Woodbine carries the name originally used by a racetrack which operated in southeast Toronto, at Queen Street East and Kingston Road, from 1874 through 1993.

Taylor, began a program of racetrack acquisitions aimed at becoming the biggest and most profitable operator in Ontario horse racing, similar to Taylor's earlier acquisitions and consolidations in the Canadian brewing industry.

[4] Renovations began immediately at Fort Erie and at Woodbine, financed by a public offering of stock for CA$2 million.

The OJC continued the Canadian International and Cup and Saucer stakes races that had been held at the Orpen tracks.

In 1952, the OJC identified the new location of the racetrack at Highway 27 east of the Toronto airport and bought over 400 acres (160 ha).

The grandstand, designed to get as many people as close to the finish line as possible, included several restaurants and cafeterias.

[12] In 2022, Woodbine announced plans to add an 8,000-seat soccer-specific stadium and adjoining training facilities in the northeast corner of the property; this would be the presumed new home of York United FC and possibly house a future professional women's soccer club.

It was then converted to a crushed limestone dirt course and was used for harness racing until April 2018.

[17] The first race on the new Inner Turf was run on June 28, 2019 and was won by Bold Rally with Eurico Rosa da Silva aboard.

The incidents include a breakdown of an unnamed horse during a workout, the 3-year-old filly Social Dancer (Society's Chairman)'s awkward step at the half-mile marker and in the GIII Bessarabian Stakes, the 6-year-old mare Owen's Tour Guide (Tourist)'s wrong step, resulting in their euthanasia.

[19] Casino Woodbine opened in 1999, offering a slots parlor and later expanded to table games in 2018.

In 2019, construction began to expand the casino to include an entertainment venue, retail shops and a hotel.

Woodbine was also the host of the CA$1,500,000 North America Cup for three-year old pacing colts and geldings from 1994–2006.

That race along with the Elegant Image Stakes for three-year old filly trotters and the Good Times Stakes for three-year old colt and gelding trotters, have been moved to Woodbine's sister track, Woodbine Mohawk Park.