How many times have Canadian NHL teams won the Stanley Cup?

Hockey and Canada go hand in hand. If it wasn’t for Canada there would be no hockey. If it wasn’t for hockey, well, Canada just wouldn’t be the same. There is a rich history of Stanley Cup success and Canadian teams in the NHL, but it’s been decades since they lifted the Cup North of the Border.

Montreal: the motherland of ice hockey

The roots of the game are deeply seeded in the Canadian provinces. It makes sense that ice hockey was birthed in Montreal, where it constantly snows and the ponds freeze over for five or six months of the year. Taking your skates and stick out is a right of passage for any Canadian kid who has dreams of making it to the NHL.

Montreal isn’t just credited with being the birthplace of the sport. They back it up with a long lasting tradition of winning, as any place who invented a sport should. The Montreal Canadiens are the winningest franchise in the NHL, having won 24 Stanley Cups throughout their illustrious history. They won the first Stanley Cup ever back in 1916 when they took the National Hockey Association title and played the Portland Rosebuds who won the Pacific Coast Hockey Association. The series went to all five games, but it was the Canadiens who had their name etched on the Cup first.

Montreal would go on to win 23 more Stanley Cups, once in the 20′s, twice in the 30′s, twice in the 40′s, but the fifties is when they really solidified their position as a powerhouse of the sport. Guys like Jaques Plante, Jean Believeau, Bernie Geoffrion, Richard Henry and Dickie Moore led the Canadians to a dynasty. They won it all 1953, and and then won five straight Stanley Cups from 1956-1960.

Canadiens set the standard from early on

The Dynasty wouldn’t end there. Montreal won Lord Stanley’s Cup four more times in the 60′s and then six times in the 70′s including going back-to-back-to-back-to-back from 1976 to 1979. Since then the Canadiens have gone on a drought that must be driving the locals out of their minds. They won it in 1986 and got their last one in 1993. There is a whole generation of Montreal fans that have never seen their team as the last man standing after the Stanley Cup Playoffs, something that their parents and grandparents could never have fathomed.

As we look down the list of the winningest franchises in the NHL, we will stay north of the border. The Toronto Maple Leafs are second in all time Stanley Cups won, with 13. The Leafs won the third ever Stanley Cup in 1918 against the Vancouver Millionaires of the Pacific Coast Hockey Association. They would go on to to win three more over the next quarter of a century, but in the last half of the 1940′s Toronto turned into a dynasty, winning five Cups from 1945 to 1951 with Turk Broda in goal, Bill Barilko as a defenseman and Ted Kennedy as the center.

Toronto fans would have to wait for over decade until their next Stanley Cup win in the 1962. They would win four in six years to make up for lost time, but since 1967 the Maple Leafs have gone cold. Not only have they not won the Cup but they haven’t made it to the Finals since beating the Canadiens back in ‘67.

The Great One leads Oilers to greatness in the 80′s

The Americans finally appear on the list at spots 3-5, with the Detroit Red Wings’ 11, Bostons’ six and Chicago’s six sitting right above the Edmonton Oilers who have won five total Stanley Cups.

The Oilers joined the NHL in 1979 and didn’t take long to start dominating the league. Five years after jumping ships to the NHL they won their first Stanley Cup against the New York Islanders in 1984. They made it back-to-back bids the season after when they beat the Philadelphia Flyers for their second Stanley Cup.

It should come as no surprise that the Oilers golden years came at a time when they had hockey’s Golden Boy, Wayne Gretzky. Gretzky was in Edmonton for four of the five titles in the history of the franchise. Those four titles were won in a span of five years, from 1984 to 1988.

Gretzky would change airs from Edmonton to LA after winning the fourth Stanley Cup for the Oilers, but that didn’t mean the Oilers were done winning. Mark Messier took over captain duties and led Edmonton to their fifth and final title two years later.

Vancouver, Ottowa and Winnepeg still without a Stanley Cup

The last Canadian team on the list is the Calgary Flames who have won just once since they moved form Atlanta to Calgary in 1980. Their sole Stanley Cup came right after Gretzky left Edmonton. After reaching the Finals only to have their hearts broken by the Canadiens in the 1986 season the Flames made it back to the Finals four years later when they avenged their loss to Montreal.

There are three other Canadian teams that are still searching for their first Stanley Cup ever. The Vancouver Canucks are the longest standing team without a title, having joined the NHL in 1970. They have made it to the Finals three different times but came up empty on each occasion. The Ottawa Senators joined the League in 1992, and got to the Finals in 2007 but have never broken through to win the Cup. Finally the Winnipeg Jets, who flirted with the Stanley Cup Finals just one since moving from Atlanta, and rebranding the franchise in 2011.

Canada is desperate for the Stanley Cup to return. Even though these Canadian teams are considered rivals, fans from the same country will be rooting on their countrymen even if their teams fails to make it to the Finals. It remains to be seen, but the drought has stretched to nearly 30 years since a team north of the border won it all.