| Valley 3, The Classical Academy 0 | Aug. 30 | Details |
| Manitou Springs High School 3, The Classical Academy 2 () | Sept. 11 | Details |
| The Classical Academy 3, Florence 0 () | Sept. 13 | Details |
| Cherry Creek 2, The Classical Academy 0 | Sept. 15 | Details |
| Pomona High School 2, The Classical Academy 1 | Sept. 15 | Details |
| Lakewood High School 2, The Classical Academy 0 | Sept. 15 | Details |
| The Classical Academy 2, Horizon 0 | Sept. 15 | Details |
| The Classical Academy 3, Fountain Valley 0 () | Sept. 17 | Details |
| The Classical Academy 3, Buena Vista 0 () | Sept. 20 | Details |
| The Classical Academy 3, Colorado Springs Christian School 1 () | Sept. 25 | Details |
| Air Academy High School 3, The Classical Academy 1 | Sept. 27 | Details |
| The Classical Academy 3, Salida 0 () | Oct. 2 | Details |
| Manitou Springs High School 3, The Classical Academy 2 () | Oct. 4 | Details |
| The Classical Academy 3, Florence 0 () | Oct. 9 | Details |
| The Classical Academy 3, Fountain Valley 0 () | Oct. 11 | Details |
| The Classical Academy 3, Buena Vista 0 () | Oct. 16 | Details |
| The Classical Academy 3, Colorado Springs Christian School 2 () | Oct. 18 | Details |
| The Classical Academy 3, Salida 0 () | Oct. 23 | Details |
| The Classical Academy 2, La Junta 0 | Oct. 27 | Details |
| The Classical Academy 2, Fountain Valley 0 | Oct. 27 | Details |
| The Classical Academy vs. St. Mary's at Colorado Springs Christian School | Oct. 27 @ 4:30 p.m. | Map |
| Manitou Springs High School 2, The Classical Academy 1 | Oct. 27 | Details |
| Sterling 3, The Classical Academy 2 | Nov. 3 | Details |
| The Classical Academy 3, Clear Creek High School 0 | Nov. 3 | Details |
