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This is the 1999-00 Highway Hockey League season. This is the league's 35th season.
- A team from Soo Line is added to the league
- The Dysart Blues leave the league
|Semans Wheat Kings||24||13||9||2||0||28||106||95||704|
- Lumsden defeated Cupar 3 games to 2 (3-5, 6-4, 4-7, 7-6, 5-2)
- Raymore defeated Southey 3 games to 1 (4-5, 5-1, 5-1, 6-3)
- Raymore defeated Lumsden 4 games to 2 (5-4, 7-3, 4-5, 3-2, 9-5, 5-2)