Hart helped lead the team to three Stanley Cups, in 1924, 1930, and 1931. He was fired after a dispute with Canadiens' owner Léo Dandurand after leading the Canadiens to first place in the 1931-32 season, but after Dandurand and Joseph Cattarinich sold the Canadiens to Ernest Savard and Maurice Forget of the Canadian Arena Company, the Canadiens hit bottom in 1935-36.
To rebuild the team, they rehired Hart in 1936-37, but Hart would only come back if Howie Morenz did. A deal was arranged and with Morenz back, and despite the death of Morenz during the season, Hart managed to lead the Canadiens to first place. After that, the team eroded as age caught up with some key players. When the Canadiens were reclining near the cellar in 1938-39, Cecil resigned as coach and manager. Only eighteen other people have won multiple Stanley Cups besides Hart as a head coach, although he is not currently inducted into the Hockey Hall of Fame despite being eligible. 
Hart later became vice president and treasurer of the Quebec, Ontario and Vermont Baseball League also before his untimely death.
|Team||Year||Regular season||Post season|
|Montreal Canadiens||1926-27||44||28||14||2||58||2nd in Canadian||Lost in Semi-Finals|
|Montreal Canadiens||1927-28||44||26||11||7||59||1st in Canadian||Lost in Semi-Finals|
|Montreal Canadiens||1928-29||44||22||7||15||59||1st in Canadian||Lost in Semi-Finals|
|Montreal Canadiens||1929-30||44||21||14||9||51||2nd in Canadian||Won Stanley Cup|
|Montreal Canadiens||1930-31||44||26||10||8||60||1st in Canadian||Won Stanley Cup|
|Montreal Canadiens||1931-32||48||25||16||7||57||1st in Canadian||Lost in Semi-Finals|
|Montreal Canadiens||1936-37||48||24||18||6||54||1st in Canadian||Lost in Semi-Finals|
|Montreal Canadiens||1937-38||48||18||17||13||49||3rd in Canadian||Lost in Quarter-Finals|
|Montreal Canadiens||1938-39||30||6||18||6||(18)||6th in NHL||(Fired)|