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
Standings[]
| GP | W | L | OL | T | PTS | GA | GA | PIM | |
| Cupar Canucks | 24 | 18 | 5 | 1 | 0 | 37 | 168 | 89 | 574 |
| Raymore Rockets | 24 | 17 | 5 | 1 | 1 | 36 | 137 | 78 | 980 |
| Southey Marlins | 24 | 15 | 7 | 0 | 2 | 32 | 116 | 77 | 993 |
| Lumsden Monarchs | 24 | 14 | 7 | 2 | 1 | 31 | 128 | 97 | 672 |
| Semans Wheat Kings | 24 | 13 | 9 | 2 | 0 | 28 | 106 | 95 | 704 |
| Soo Line | 24 | 4 | 20 | 0 | 0 | 8 | 75 | 164 | 717 |
| Strasbourg Maroons | 24 | 1 | 23 | 0 | 0 | 2 | 55 | 185 | 934 |
Playoffs[]
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)