Bobby Dawson memorably won the “Little Grey Cup” and Grey Cup trophies in back-to-back seasons. He played in four Grey Cup Games, winning two, across seven seasons in the Canadian Football League with the Hamilton Tiger-Cats.

Dawson was born in Windsor on February 4, 1932.

He attended Hugh Beaton Elementary School and split his secondary school years between Walkerville Collegiate Institute (1946-47) and W. D. Lowe Vocational (’47-50). At Walkerville, Dawson played Senior football and Junior basketball as a Grade 9 student. Later, at Lowe, he played halfback and quarterback under football coach Johnny Murray, earning honourable mention in the ’49 All-City voting. Dawson also played basketball and one year of hockey in high school. A defenceman on the ice, Dawson lined up with the future NHL star Glen Skov and eventual Windsor Bulldogs Bobby Brown and Joe Zorica.

Dawson played both football and basketball outside of the school. He won back-to-back Ontario Championships with the Windsor AKO Juniors basketball team in 1951 and ’52. In the latter year, Dawson’s team also took the Eastern Canadian Championship.

On the gridiron, Dawson played both halfback and quarterback and led Windsor AKO in scoring in 1950 and ’51. In ’52, Windsor captured the “Little Grey Cup” – the Canadian Junior Championship – by defeating the Edmonton Wildcats 15-12. Dawson’s team had trailed 12-7 after three quarters but executed a rousing come-from-behind victory. The stands were littered with CFL scouts that day, and Hamilton, Ottawa, and Saskatchewan offered Dawson professional tryouts. He chose Hamilton due to its proximity to Windsor.

In the CFL, Dawson was named Big Four Rookie of the Year in his first year and played seven total seasons as a defensive halfback with the Tiger-Cats. He contested four Grey Cups (1953, ’57, ’58, and ’59), winning the first two. All four games were played against the Winnipeg Blue Bombers. He is possibly the only player to ever win the Little Grey Cup and the full Grey Cup in two consecutive seasons.

On October 20, 1956, Dawson participated in a historically significant Tiger-Cats loss in Montreal that saw 23 total CFL records broken. With the Alouettes leading 68-7 in the third quarter, Hamilton coach Jim Trimble decided to remove regular quarter back Tony Curcillo, an Ohio State alum, who was playing with a cast on his left wrist. He inserted Dawson at quarterback for the remainder of the game, which was an unusual decision in an era in which all the top CFL quarterbacks were Americans. “Should I play for the win or tie?” Dawson allegedly asked Trimble before stepping onto the field. Ultimately, Dawson acquitted himself well, completing five of eight passes and connecting on a touchdown pass to Davey West. The game finished 82-14.

Dawson retired from CFL play following the 1959 season. He went on to coach the Burlington Braves in the ’60 ORFU Junior League, losing to Windsor AKO in the finals.

From 1961 to ’66, he coached the McMaster University Marauders in the Ontario College Conference (OCC), and Ontario Intercollegiate Athletic Association (OIAA). Dawson’s Marauders won five consecutive league championships. At that time, McMaster played in a league with Carleton, Ottawa, Waterloo, Waterloo Lutheran, Guelph, Montreal, Loyola, and the Royal Military College. Dawson twice took his team to the Atlantic Bowl, which matched the AUAA champions against the OCC or OIAA champions. McMaster won once and lost once.