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This is the 1999-00 North Central Hockey League season, the league's 43rd season.
Hamiota defeated Kenton 2-games-to-none
- Preliminary Round
Miniota defeated Hamiota 3-games-to-none
Oak Lake defeated McCreary 3-games-to-1
Minnedosa defeated Virden 3-games-to-1
Blanshard defeated Elkhorn 3-games-to-2
- Quarter Finals
Miniota defeated Oak Lake 3-games-to-1
Minnedosa defeated Blanshard 3-games-to-2
- Semi Finals
Miniota defeated Minnedosa 3-games-to-none