The school offers both semestered and full year courses, in a blended system called Moduflex.

During the late 1960s and the early 1970s, Morris the Mustang, the school's mascot,[1] would be paraded around South Windsor's Norfolk Street to celebrate the commencement of the football season.

By the 1980s, the demographics of South Windsor changed greatly and the baby boom population had moved on, leaving Massey with approximately 800 students.

In 2000, Vincent Massey welcomed students from W. D. Lowe High School after it closed down in June of that year.

Located in the heart of the South Windsor neighbourhood, the campus sits on approximately five acres of land.

[3] Vincent Massey is one of the three schools within Windsor that offers the Advanced Placement program for senior students.

[7] Mathematics teacher Christopher Ing, who is a former Massey student as well as former pupil of Bruce White, was one of the recipients of the High School Sliffe Award in 2008.

[9] Ferrara was also selected by the Ontario Ministry of Education, as the high school teacher representative, to the Financial Literacy Working Group.

As of the 2015–16 season Massey has won a total of 11 consecutive WECSSAA Cross Country Championship titles.

In the 1988–89 season, the Senior Boys Football Team nearly got a "three-peat" but lost the city championship in an infamous triple over-time game when they missed a last minute field goal attempt.

These teams were "co-coached" by both Brian Tayles (former head coach for the Centennial Cougars) and Godfrey Janisse (long time Massey Mustang head coach) with Tayles running the Offense and Janisse running defense and special teams.

In the 1987–88 season, the Senior Girls Soccer Team won the city championship., In the 1987–88 season, the Senior Boys Soccer Team won the city and the Essex County championship, having the Brazilian exchange student Paulo Soares (nicknamed PIPO) as their international star.

In the 1990–91 season, the Senior Boys Soccer Team again won the city championship in a dramatic penalty shootout against the Lowe Trojans.