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.
Expansion
Brampton Battalion
On December 3, 1996, the Brampton Battalion was granted an expansion franchise owned by Scott Abbott. The team began play in the 1998–99 season, playing in the Midwest Division of the Western Conference. The Battalion's arena was the newly constructed Brampton Centre.
Brampton played in their first game on September 24, 1998, losing 5–1 to the Peterborough Petes on the road. Their first home game was on October 9, as the Battalion dropped a 5-1 decision to the Kitchener Rangers in front of a sold-out crowd of 4,800 at the Brampton Centre. After beginning the season with six losses, Brampton won their first game, defeating the Sudbury Wolves 5–4 on October 18.
Mississauga IceDogs
On January 21, 1997, the Mississauga IceDogs was granted an expansion franchise which included former Boston Bruins head coach Don Cherry in their ownership group. The IceDogs began play in the 1998–99 season, playing in the Central Division of the Eastern Conference. The IceDogs arena was the newly constructed Hershey Centre.
The IceDogs played in their first game on September 25, 1998, losing a road game to the Kingston Frontenacs by a score of 10–0. Mississauga began the season with an 11-game road trip, as the club lost each game. In their home opener on October 30, Mississauga recorded their first win in franchise history, defeating the Toronto St. Michael's Majors 4–3 in front of a sold out of 6,000 fans at the Hershey Centre.
Realignment
With the Brampton Battalion and Mississauga IceDogs joining the Ontario Hockey League for the 1998–99 season, the league underwent a massive realignment in which two new conferences, the Eastern Conference and Western Conference, were created. Within each conference was two five-team divisions. The playoff format changed that the top eight teams in each conference made the post-season.
Note: DIV = Division; GP = Games played; W = Wins; L = Losses; T = Ties; OTL = Overtime losses; GF = Goals for; GA = Goals against; PTS = Points; x = clinched playoff berth; y = clinched division title; z = clinched conference title
Note: GP = Games played; Mins = Minutes played; W = Wins; L = Losses: OTL = Overtime losses; SL = Shootout losses; GA = Goals Allowed; SO = Shutouts; GAA = Goals against average[2]
Note: GP = Games played; Mins = Minutes played; W = Wins; L = Losses: OTL = Overtime losses; SL = Shootout losses; GA = Goals Allowed; SO = Shutouts; GAA = Goals against average[5]
