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- Lakefield Chiefs (1998-99 COJCHL Season Champions)
- Picton Pirates (1998-99 EBJCHL Season Champions)
- Kincardine Bulldogs (1998-99 WOJCHL Season Champions)
- Fergus Devils (1998-99 GMOJCHL Season Champions)
- Wallaceburg Lakers (1998-99 GLJHL Season Champions)
- Glanbrook Rangers (1998-99 NDJCHL Season Champions)
- Lakefield Chiefs defeated Picton Pirates 4-games-to-1
- Kincardine Bulldogs defeated Fergus Devils 4-games-to-3
- Wallaceburg Lakers defeated Kincardine Bulldogs 4-games-to-1
- Glanbrook Rangers defeated Lakefield Chiefs 4-games-to-1