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In the ORFU, the Sarnia Imperials had been a dominant team throug the 1930s, but now were without their star players of the era as Hugh Stirling retired prior to the season to join Norm Perry and Ormond Beach on the sidelines. The Imperials surprised many by finishing second in the ORFU and then upsetting the first place Montreal Westmounts in the ORFU final. The Westmounts were another renamed Montreal team. Having played in 1938 as the Nationals, the team moved across the city to Westmount Athletic Stadium where the Winged Wheelers used to play and took up thei rnew nick name. While the Westmounts had much better success in the regular season than their Big Four brothers, the Royals, they went down to defeat at the hands of Sarnia in the playoffs as the Imperials capitalized on several Westmount fumbles.
Out West, the Winnipeg Blue Bombers under coach Reg Threfall and with stars like Fritz Hanson were the class of the league. Regina finished second and the Calgary Bronks third. The Bronks would play one more season in 1940, and be reborn after the war in 1945 as the Stampeders. The Bronks upset Regina in the West Semi-Final, but were no match for the powerful Bombers in the final.
Back East, the Big Four champion Ottawa Rough Riders steam rollered over the ORFU Sarnia Imperials in the East Finals to set up an Ottawa vs. Winnipeg Grey Cup. The 1939 Grey Cup was played on a cold and frozen field at Lansdowne Park in Ottawa. It was hardly an offensive display by either team with 17 punts by Arnie McWatters of the Rough Riders and 16 by Greg Kabat and Al Stevenson of the Bombers. Ottawa held Fritz Hanson pretty much in check and Winnipeg completed only one of eight pass attempts. With the score tied at seven late in the fourth quarter, Stevenson punted and Orville Burke fumbled with Jeff Nicklin of the Bombers pouncing on the ball at the Ottawa 34. Ottawa stopped the Bombers and Stevenson punted into the endzone where Burke punted it out, but it went off the side of his foot and out of boudns at the Ottawa 9. With just 48 seconds left, Stevenson punted on first down and through the endzone for a single point and a 8-7 Winnipeg victory.