Best Answer #97: As no suitable answer was received, here is the Quiz Committee's:
William "Jerry" Laflamme, born in Woodstock, captained the (Toronto) St. Michael's College hockey team in 1910 when they won the Ontario Hockey Association championship and then the Allan Cup. In 1917, he captained the Toronto Dentals when they also won the Allan Cup.

Extra Information From Quiz Committee:
In his early years, Jerry Laflamme played on the Woodstock Collegiate Institute hockey team. He went on to study at St. Michael's College in Toronto, and also joined its hockey team.

After graduating, Dr. Laflamme helped found the Toronto Granites Hockey Club in 1918. The Granites went on to win the Senior Ontario Hockey association title; and then the Allan Cup in 1922 and in 1923. The Granites went on to represent Canada at the 1924 Winter Olympics in Chamonix, France. Though Laflamme coached them in 1923, he had to turn down coaching them for the Olympics: he was too busy refereeing in the National Hockey League.

In 1929, Laflamme coached the Montreal Maroons to the Stanley Cup finals (despite that, they lost to the Boston Bruins). Then in 1933 he coached two St. Michael's College teams to victory: the Majors, which won the Memorial Cup; the Buzzers, which won the Ontario Hockey Association championship. Finally, after coaching the London Mohawks, Laflamme retired in 1939.

The Stanley Cup was originally donated by Lord Stanley, the Canadian Governor-General, in 1893. His guideline was simply that the cup should go to the leading hockey club in Canada. At that time hockey was an amateur sport, and it was the Montreal Amateur Athletic Club that won the cup first.

In time, the prestige of fielding a winning hockey team pushed communities to move towards hiring professional players. By the late 1920s, winning the Stanley Cup became solely the target of the professional teams of the, then, recently-formed National Hockey League.

In the early 1900s, senior hockey players either turned pro, or ceased to play, which tended to discourage amateur hockey. To offset this and provide an incentive to amateur players, Sir H. Montague Allan, C.V.O., donated the Allan Cup in 1908. Rules and regulations were set up to ensure it could only be won by the best amateur hockey team. Its first winner, in 1908, was the Ottawa Cliffsides.

Sources:
Text:
- 'For the glory of the game - Sports Heroes of Woodstock and Oxford County,' (Woodstock Museum)
Internet:
- http://www.pittpens.clara.net/nhl/stanleycup/stanley.html - Stanley Cup story
- http://www.bordercity.com/allancup/history.htm, - Allan Cup story and winners since 1908