| 1898 (0-1) | 1919 (2-5) | 1927 (5-3) |
| Litchfield 0-15 | @ Eastern Ill.Univ. 0-51 | Assumption 26-0 |
| Alton 43-0 | Mattoon 7-13 | |
| 1899 (0-2-2) | Girard 0-38 | @ Pana 14-12 |
| @ Litchfield 0-0 | @ Waverly (Loss with no score reported) | @ Taylorville 20-0 |
| Western Military Academy of Alton 5-5 |
Mattoon 6-14 | Mt. Olive 6-0 |
| @ Irving 0-29 | @ Taylorville 6-58 | Nokomis 0-3 |
| Greenville 5-10 | Litchfield 62-13 | Staunton 0-14 |
| @ Litchfield 12-0 | ||
| 1900 (2-0-1) | 1920 (5-4) | |
| Litchfield 17-0 | @ Pana 6-0 | 1928 (2-6-1) |
| Coffeen 0-0 | @ Mattoon 0-38 | @ Greenville 19-6 |
| Greenville 6-5 | Stonington 13-20 | @ Mattoon 19-6 |
| Gillespie 31-0 | Benld 6-13 | |
| 1901 (3-1) | Shelbyville 72-0 | Pana 12-6 |
| Jacksonville ISO 0-36 | Staunton 20-7 | @ Mt. Olive 6-6 |
| Western Military Academy of Alton 15-0 |
Staunton 0-7 | @ Nokomis 2-3 |
| @ Litchfield 22-0 | @ East St. Louis 0-18 | @ Staunton 0-18 |
| Greenville 6-0 | @ Litchfield 13-0 | Carlinville 0-12 |
| Litchfield 0-7 | ||
| 1902 (3-2) | 1921 (5-3) | |
| @ Jacksonville ISO 0-21 | @ Girard 28-0 | 1929 (7-0-1) |
| Pana 12-0 | Pana 14-3 | Greenville 33-0 |
| @ Western Military Academy of Alton 0-18 |
@ Shelbyville 28-0 | Taylorville 7-6 |
| Raymond 45-0 | Benld 21-7 | @ Carlinville 13-6 |
| Litchfield (Forfeit Win) | East St. Louis 7-34 | Gillespie 13-6 |
| @ Gillespie 0-14 | Nokomis 29-0 | |
| 1903 (3-3) | Mattoon 0-24 | Staunton 57-0 |
| @ Jacksonville ISO 0-6 | Litchfield 6-0 | Mt. Olive 0-0 |
| Pana 11-0 | @ Litchfield 23-0 | |
| @ Coffeen 12-0 | 1922 (5-2) | |
| @ Greenfield 0-11 | Girard 7-6 | 1930 (7-0-1) |
| Western Military Academy of Alton 0-6 |
@ Pana 21-12 | @ Taylorville 26-0 |
| Greenville 23-0 | Mt. Olive 0-26 | @ Mt. Olive 33-0 |
| Gillespie 6-0 | @ Nokomis 26-0 | |
| 1904 (2-3) | @ Mattoon 0-25 | @ Shelbyville 6-0 |
| Raymond 26-0 | Edwardsville 54-7 | @ Staunton 0-0 |
| Carrollton 0-35 | Shelbyville 61-0 | Gillespie 33-0 |
| @ Alton 0-70 | @ Pana 12-0 | |
| @ Jacksonville ISO 0-34 | 1923 (5-3) | Litchfield 12-0 |
| Bunker Hill Military Academy 11-5 |
Benld 0-26 | |
| @ Edwardsville 26-6 | 1931 (5-2-1) | |
| 1905 (3-3-2) | Mattoon 8-6 | @ Kincaid (Forfiet Loss) |
| @ Irving 0-2 | Pana 7-30 | @ Granite City 21-0 |
| Irving 6-6 | @ Gillespie 21-0 | Mt. Olive 47-0 |
| @ Donnellson 12-5 | Assumption 7-38 | Nokomis 0-0 |
| @ Bunker Hill Military Academy 6-0 |
Mt. Olive 21-0 | @ Gillespie 16-0 |
| @ Taylorville 0-0 | @ Litchfield 10-0 | Staunton 12-13 |
| Donnellson 17-0 | Pana 52-0 | |
| Bunker Hill Military Academy 0-11 |
1924 (7-0-1) | @ Litchfield 14-6 |
| H.H.S. Alumni 0-11 | @ Mattoon 7-0 | |
| Edwardsville 32-0 | 1932 (8-0-1) | |
| Hillsboro Dropped Football From 1906 Through 1915. |
@ Girard 35-0 | Girard 19-6 |
| Gillespie 72-0 | Granite City 0-0 | |
| 1916 (2-3) | @ Mt. Olive 16-6 | @ Nokomis 7-0 |
| MT. Olive 3-44 | Shelbyville 13-0 | Gillespie 7-0 |
| @ Morrisonville 39-0 | @ Staunton 0-0 | @ Taylorville 32-0 |
| Assumption 19-12 | Litchfield 72-0 | @Mt.Olive 27-6 |
| @ Western Military Academy of Alton 13-26 |
Carlinville 14-0 | |
| Litchfield 0-31 | 1925 (5-2) | @ Staunton 24-0 |
| Mattoon 26-0 | Litchfield 14-6 | |
| 1917 (4-2) | Gillespie 17-0 | |
| Morrisonville 57-0 | Nokomis 60-0 | 1933 (8-0-1) |
| @ Staunton 26-0 | @ Carlinville 10-17 | @ Nokomis 19-0 |
| @ Pana 7-39 | Staunton 0-32 | Peoria Manual 6-6 |
| @ Mt. Olive 20-13 | Mt. Olive 10-6 | @ Carlinville 7-6 |
| @ Girard 20-13 | @ Litchfield 25-0 | @ Granite City 15-0 |
| @ Litchfield 16-12 | @ Gillespie 9-6 | |
| 1926 (4-2-1) | Carlyle 70-0 | |
| 1918 (1-0) | Pana 0-6 | Nokomis 28-6 |
| Benld 25-18 | @ Mt. Olive 0-16 | Staunton 13-0 |
| Gillespie 12-0 | Pana 34-0 | |
| @ Mattoon 0-0 | ||
| @ Staunton 7-0 | ||
| @ Nokomis 6-2 | ||
| Litchfield 14-6 |