After retaining the Eastern Canada Amateur Hockey Association crown with an 8-2-0 record, the Wanderers faced the Winnipeg Maple Leafs, champions of the Manitoba Hockey League.
For the first time in Stanley Cup play, every man on the winning team except the goalie scored at least once as the Wanderers took the first game. In the second game, Bruce Stuart and Ernie Johnson each registered four goals.
The Toronto "Trolley Leaguers", champions of the OPHL, the first entirely pro hockey league ever formed in Canada, played the Wanderers in a one-game, sudden-death affair.
The see-saw battle included four ties until Ernie Johnson scored the Wanderers' game-winning goal and Bruce Stuart tallied an insurance marker.
In his premier Stanley Cup appearance, Newsy Lalonde scored twice for Toronto.
1907-08 - Montreal Wanderers - Riley Hern, Art Ross, Walter Smaill, Frank (Pud) Glass, Bruce Stuart, Ernie Russell, Ernie (Moose) Johnson, Cecil Blachford (captain), Tom Hooper, Larry Gilmour, Ernie Liffiton, R.R. Boon (manager).
SCORES
| Mar. 10 | Wpg. Maple Leafs | 5 | at Mtl. Wanderers | 11 |
| Mar. 12 | Wpg. Maple Leafs | 3 | at Mtl. Wanderers | 9 |
| Mar. 14 | Toronto | 4 | at Mtl. Wanderers | 6 |