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The 1998–99 OHL season was the 19th season of the Ontario Hockey League. The Brampton Battalion and the Mississauga IceDogs were added as expansion teams. The league realigned from three divisions into two conferences and four divisions. Brampton were placed in the Midwest division of the Western conference, and Mississauga were placed in the Central division of the Eastern conference. The OHL inaugurated four new trophies this season. The Holody Trophy was created for the regular season champion of the Midwest division. Two conference playoffs champions were created; the Bobby Orr Trophy for the Eastern conference, and the Wayne Gretzky Trophy for the Western conference. The fourth new trophy was the Wayne Gretzky 99 Award, to be awarded to the MVP of the playoffs. Twenty teams each played sixty-eight games. The Belleville Bulls won the J. Ross Robertson Cup, defeating the London Knights.
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