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| 1920 | OA |
| Laramie | 4-2 |
| Sheridan | 4-2 |
| Natrona | 3-2 |
| Cheyenne Central | 4-3-2 |
| Newcastle | 1-3 |
| Buffalo | 0-1 |
| University Prep | 0-4-1 |
| 1919 | OA |
| Sheridan | 4-1 |
| Laramie | 2-1 |
| Cheyenne Central | 2-2 |
| Buffalo | 0-1 |
| Natrona | 0-1 |
| 1918 | OA |
| No games played | – |
| 1917 | OA |
| Sheridan | 7-0 |
| Laramie | 1-1-1 |
| Cheyenne Central | 0-4-1 |
| Buffalo | 0-2 |
| 1916 | OA |
| Laramie | 3-0-3 |
| Sheridan | 2-2-1 |
| Buffalo | 0-1 |
| Cheyenne Central | 0-2 |
| 1915 | OA |
| Sheridan | 3-3 |
| Laramie | 3-5 |
| Cheyenne Central | 1-2 |
| 1914 | OA |
| Wheatland | 2-1 |
| Cheyenne Central | 2-4 |
| Sheridan | 1-2 |
| Douglas | 0-2 |
| 1913 | OA |
| Douglas | 2-0 |
| Sheridan | 1-0 |
| Cheyenne Central | 5-0-1 |
| Wheatland | 0-2 |
| 1912 | OA |
| Sheridan | 3-1-1 |
| Cheyenne Central | 4-4-1 |
| Natrona | 1-1 |
| Wheatland | 0-2 |
| Laramie | 0-3 |
| 1911 | OA |
| Sheridan | 4-0 |
| Laramie | 2-2-1 |
| Cheyenne Central | 0-3 |
| 1910 | OA |
| Fort Washakie | 2-0 |
| Laramie | 1-1-1 |
| Sheridan | 1-1 |
| Lander | 1-2-1 |
| Natrona | 0-1-1 |
| Cheyenne Central | 0-3-1 |
| 1909 | OA |
| Natrona | 2-1 |
| Cheyenne Central | 3-2-1 |
| Douglas | 1-3 |
| Laramie | 1-4 |
| University Prep | 0-1 |
| 1908 | OA |
| Laramie | 1-0 |
| Cheyenne Central | 4-1 |
| Natrona | 1-0-1 |
| Lander | 0-0-1 |
| Douglas | 0-1 |
| University Prep | 0-3 |
| 1907 | OA |
| Cheyenne Central | 1-7 |
| 1906 | OA |
| Cheyenne Central | 0-0-2 |
| 1905 | OA |
| Cheyenne Central | 1-2-2 |
| 1904 | OA |
| Cheyenne Central | 1-2-1 |
| 1903 | OA |
| Laramie | 0-1 |
| 1902 | OA |
| Cheyenne Central | 0-1 |
| 1901 | OA |
| Laramie | 1-1 |
| 1898-1900 | OA |
| No games played | – |
| 1897 | OA |
| Laramie | 0-1 |
| 1896 | OA |
| Laramie | 0-1 |
| 1895 | OA |
| Laramie | 0-2 |
| 1894 | OA |
| Cheyenne Central | 0-1 |