| The Classical Academy 3, Mesa Ridge High School 2 | Aug. 30 | Details |
| The Classical Academy 3, Manitou Springs High School 2 () | Sept. 4 | Details |
| The Classical Academy 2, Fossil Ridge 0 | Sept. 8 | Details |
| The Classical Academy 2, Erie 0 | Sept. 8 | Details |
| The Classical Academy 2, Lutheran (Denver) 0 | Sept. 8 | Details |
| Basalt 2, The Classical Academy 1 | Sept. 8 | Details |
| The Classical Academy 3, Florence 0 () | Sept. 11 | Details |
| The Classical Academy 3, Florence High School 0 () | Sept. 11 | Details |
| Colorado Springs Christian School 3, The Classical Academy 0 () | Sept. 22 | Details |
| The Classical Academy 3, Lake County 0 | Sept. 27 | Details |
| The Classical Academy 3, Woodland Park High School 1 | Sept. 29 | Details |
| The Classical Academy 3, Colorado Springs Christian School 0 () | Oct. 2 | Details |
| Florence High School vs. The Classical Academy at Florence High School () | Oct. 4 @ 4 p.m. | Map |
| The Classical Academy 3, Florence 0 () | Oct. 4 | Details |
| Manitou Springs High School 3, The Classical Academy 0 () | Oct. 9 | Details |
| The Classical Academy 3, Lake County 0 | Oct. 19 | Details |
| Buena Vista 3, The Classical Academy 1 | Oct. 20 | Details |
| The Classical Academy 3, St. Mary's 1 | Oct. 27 | Details |
| The Classical Academy 3, Platte Valley 0 | Nov. 3 | Details |
| The Classical Academy 3, Monte Vista 1 | Nov. 3 | Details |
| The Classical Academy 3, Valley 2 | Nov. 3 | Details |
| Colorado Springs Christian School 3, The Classical Academy 2 | Nov. 9 | Details |
| The Classical Academy 3, Lamar 0 | Nov. 9 | Details |
| Colorado Springs Christian School vs. The Classical Academy at Colorado Springs Christian School | Nov. 10 @ 11:02 p.m. | Map |
