1999-00 HHL Season

This is the 1999-00 Highway Hockey League season. This is the league's 35th season.

Membership changes

 * A team from Soo Line is added to the league
 * The Dysart Blues leave the league

Semifinals

 * 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)

Final

 * Raymore defeated Lumsden 4 games to 2 (5-4, 7-3, 4-5, 3-2, 9-5, 5-2)