In 1989, two Canadian male tennis players, Grant Connell and Andrew Sznajder, reached the quarterfinals of the event.

Lendl has been the tournament's most successful singles player, reaching the final nine times and winning the title in 1980, 1981, 1983, 1987, 1988, and 1989.

In 1995, Andre Agassi and Pete Sampras met in the final, the third of the four times that the two top-ranked men's players would meet that year, after the Australian Open and Indian Wells Masters.

Agassi's tournament win helped him regain the number-one ranking, which he lost to Sampras after they played each other again at the US Open.

In 1997, the Canadian federal government introduced legislation restricting the ability of tobacco companies from sponsoring sporting events.

[4] In 2000, International Sport and Leisure signed a 10-year agreement with the ATP Tour for all Masters series events, including the men's tournament.

[5] Serena Williams won the women's tournament for the first time, defeating top-seeded and previous winner Jennifer Capriati.

[5] Rafael Nadal won the men's tournament for his first time, defeating three-time champion Andre Agassi.

[7] In 2007, Novak Djokovic won the men's tournament for the first time, becoming the first man to defeat both Nadal and Roger Federer in the same event.

[9] The WTA's rules required each year-end top-10 player from 2008 to participate in at least four Premier 5 tournaments in the 2009 season, or face the threat of fines or docked ranking points.

Beginning in 2011, the men's and women's tournaments were held during the same week, with each event alternating between Montreal and Toronto.