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- Kincardine Bulldogs (1999-00 WOJCHL Season Champions)
- Fergus Devils (1999-00 GMOJCHL Season Champions)
- Lakefield Chiefs (1999-00 COJCHL Season Champions)
- Campbellford Rebels (1999-00 EBJCHL Season Champions)
- Belle River Canadiens (1999-00 GLJHL Season Champions)
- Chippawa Riverhawks (1999-00 NDJCHL Season Champions)
- Kincardine Bulldogs defeated Fergus Devils 4-games-to-3
- Lakefield Chiefs defeated Campbellford Rebels 4-games-to-none
- Belle River Canadiens defeated Kincardine Bulldogs 4-games-to-none
- Lakefield Chiefs defeated Chippawa Riverhawks 4-games-to-2