President: Major A.L. Steele M.B.E.
In January 1949 East Windsor Blues were admitted to the Ontario Major League. As they were sponsored by the Sterling Construction Company, they changed their name to Windsor Sterling. The other members of the league at the time were Toronto Scottish, Ulster United, John Inglis, Mahers and Silverthorne Legion.
In March two new clubs joined the league. These two were London Labatts and Brantford Nationals. In addition to these two teams the league now consisted of Windsor Sterlings, Ulster United, Toronto Scottish and Silverthorn Legion. Before the season started Toronto Celtic were added to the league.
Toronto Celtics was managed by Andy Stevens.
Results and standings
September 24, 1949 Wigle Park, Windsor, Ontario
Windsor Sterlings 2 (Walker, Vlajkovich)
Toronto Scottish 1 (Jim Carmichael)
October 2, 1949 Toronto
Toronto Scottish 1 (Jack MacKenzie)
Windsor Sterlings 1 (Peter Shields)
Windsor Sterlings won the two-game total-goals series 3-2
September ??, 1949 Toronto, Ontario
October 1, 1949 London, Ontario
London Labatts 1
Ulster United 5
Ulster United won the two-game total-goals series
October 8, 1949 Toronto, Ontario
Ulster United 3 (Fred Fletcher 2, John Gifford)
Windsor Sterlings 4 (Jimmy Vlajkovich 3, Tom Spratt)
October 15, 1949 Wigle Park, Windsor, Ontario
Windsor Sterlings 0
Ulster United 0
Windsor: House; Cunningham, McNichol; Spratt, Davidson, Jim Clark; Shields, Dunn, Vlajkovich, Tom Lillie, Walker. Subs: Cardno, Tomich, Dalton
Ulster: MacFarlane; Davies, Perrett; Sam Davidson, McKay, McDowall; Carnegie, Axe, Fletcher, Giffard, Ross. Subs: Miller, Aiken, Bill Davidson
Windsor Sterlings won the two-game, total points series.