| 2019-08-23 17:30:02August 23, 2019 | Defenders vs Metro United | 6 - 4 | Non-Conference | N/A | Recap |
| 2019-08-24 14:00:26August 24, 2019 | Defenders vs CCS Eagles | 3 - 3 | Christian Athletic League | N/A | Recap |
| 2019-08-26 16:30:02August 26, 2019 | New Richmond vs Jaguars | 2 - 4 | Non-Conference | N/A | Recap |
| 2019-08-27 17:30:36August 27, 2019 | CCS Eagles vs Trojans | 5 - 1 | Christian Athletic League | N/A | Recap |
| 2019-08-29 14:00:01August 29, 2019 | CCS Eagles vs Chain o Lakes | 4 - 2 | Non-Conference | N/A | Recap |
| 2019-08-29 16:30:30August 29, 2019 | CCS Warriors vs Metro United | 1 - 2 | Non-Conference | N/A | Recap |
| 2019-08-29 17:30:06August 29, 2019 | Defenders vs Jaguars | 1 - 7 | Christian Athletic League | N/A | Recap |
| 2019-09-03 16:00:46September 3, 2019 | Saints vs CCS Eagles | 1 - 3 | Christian Athletic League | N/A | Recap |
| 2019-09-07 09:30:46September 7, 2019 | CCS Warriors vs Defenders | 2 - 5 | Christian Athletic League | N/A | Recap |
| 2019-09-07 14:00:23September 7, 2019 | Jaguars vs Defenders | 5 - 1 | Christian Athletic League | N/A | Recap |
| 2019-09-09 17:00:28September 9, 2019 | CCS Warriors vs Chain o Lakes | 1 - 5 | Non-Conference | N/A | Recap |
| 2019-09-09 17:15:00September 9, 2019 | Defenders vs Coulee Region Christian School | 2 - 5 | Non-Conference | N/A | Recap |
| 2019-09-10 16:00:00September 10, 2019 | St. Francis Christian School vs CCS Eagles | 10 - 0 | Non-Conference | N/A | Recap |
| 2019-09-10 16:00:10September 10, 2019 | CCS Warriors vs SC Warriors | 3 - 7 | Christian Athletic League | N/A | Recap |
| 2019-09-12 16:30:18September 12, 2019 | Chain o Lakes vs CCS Eagles | 3 - 5 | Non-Conference | N/A | Recap |
| 2019-09-13 18:00:52September 13, 2019 | CCS Warriors vs Trojans | 5 - 7 | Christian Athletic League | N/A | Recap |
| 2019-09-14 13:30:53September 14, 2019 | SC Warriors vs Trojans | 5 - 4 | Christian Athletic League | N/A | Recap |
| 2019-09-16 16:30:47September 16, 2019 | CCS Warriors vs Jaguars | 0 - 7 | Christian Athletic League | N/A | Recap |
| 2019-09-17 16:00:48September 17, 2019 | CCS Eagles vs SC Warriors | 1 - 2 | Christian Athletic League | N/A | Recap |
| 2019-09-19 16:30:43September 19, 2019 | Jaguars vs Chisago Lakes Baptist School | 10 - 0 | Non-Conference | N/A | Recap |
| 2019-09-20 13:00:36September 20, 2019 | Lake Region Christian School vs CCS Warriors | 4 - 2 | Non-Conference | N/A | Recap |
| 2019-09-20 14:00:49September 20, 2019 | Granite City Baptist School vs Jaguars | 0 - 4 | Non-Conference | N/A | Recap |
| 2019-09-20 14:45:37September 20, 2019 | Prior Lake vs CCS Eagles | 1 - 4 | Non-Conference | N/A | Recap |
| 2019-09-20 17:30:35September 20, 2019 | Prior Lake vs CCS Eagles | 2 - 2 | Non-Conference | N/A | Recap |
| 2019-09-20 18:00:36September 20, 2019 | Granite City Baptist School vs Jaguars | 0 - 7 | Non-Conference | N/A | Recap |
| 2019-09-21 10:30:44September 21, 2019 | Saints vs Jaguars | 0 - 10 | Christian Athletic League | N/A | Recap |
| 2019-09-21 10:45:09September 21, 2019 | Lake Region Christian School vs CCS Eagles | 2 - 1 | Non-Conference | N/A | Recap |
| 2019-09-21 11:00:14September 21, 2019 | ILHS, Eau Claire vs Trojans | 3 - 2 | Non-Conference | N/A | Recap |
| 2019-09-21 21:30:59September 21, 2019 | Trek North vs CCS Warriors | 1 - 1 | Non-Conference | N/A | Recap |
| 2019-09-23 16:30:06September 23, 2019 | CCS Warriors vs Saints | 4 - 0 | Christian Athletic League | N/A | Recap |
| 2019-09-23 17:30:53September 23, 2019 | CCS Eagles vs Maplewood Academy | 3 - 4 | Non-Conference | N/A | Recap |
| 2019-09-24 16:30:48September 24, 2019 | Jaguars vs SC Warriors | 1 - 2 | Christian Athletic League | N/A | Recap |
| 2019-09-24 18:00:04September 24, 2019 | Maplewood Academy vs Trojans | 6 - 1 | Non-Conference | N/A | Recap |
| 2019-09-27 13:10:57September 27, 2019 | CCS Warriors vs Lake Region Christian School | 3 - 3 | Non-Conference | N/A | Recap |
| 2019-09-27 15:50:45September 27, 2019 | St. Francis Christian School vs CCS Warriors | 9 - 2 | Non-Conference | N/A | Recap |
| 2019-09-27 16:30:50September 27, 2019 | Jaguars vs CCS Eagles | 1 - 1 | Christian Athletic League | N/A | Recap |
| 2019-09-28 11:00:34September 28, 2019 | Trojans vs Jaguars | 0 - 9 | Christian Athletic League | N/A | Recap |
| 2019-09-28 11:00:35September 28, 2019 | CCS Warriors vs Chisago Lakes Baptist School | 2 - 3 | Christian Athletic League, Non-Conference | N/A | Recap |
| 2019-10-01 16:00:09October 1, 2019 | CCS Eagles vs CCS Warriors | 6 - 0 | Christian Athletic League | N/A | Recap |
| 2019-10-04 16:00:03October 4, 2019 | SC Warriors vs CCS Eagles | 0 - 1 | Christian Athletic League | N/A | Recap |
| 2019-10-05 13:00:59October 5, 2019 | Saints vs Trojans | 2 - 4 | Christian Athletic League | N/A | Recap |
| 2019-10-05 15:00:42October 5, 2019 | Defenders vs Saints | 5 - 3 | Christian Athletic League | N/A | Recap |
| 2019-10-07 16:30:32October 7, 2019 | Jaguars vs CCS Warriors | 2 - 0 | Christian Athletic League | N/A | Recap |
| 2019-10-07 18:00:15October 7, 2019 | Trojans vs Maplewood Academy | 1 - 10 | Non-Conference | N/A | Recap |
| 2019-10-08 16:00:58October 8, 2019 | CCS Eagles vs Saints | 5 - 1 | Christian Athletic League | N/A | Recap |
| 2019-10-08 16:45:13October 8, 2019 | Owatonna Christian School vs Defenders | 2 - 6 | Non-Conference | N/A | Recap |
| 2019-10-10 16:00:07October 10, 2019 | CCS Warriors vs CCS Eagles | 0 - 4 | Christian Athletic League | N/A | Recap |
| 2019-10-11 16:30:52October 11, 2019 | Jaguars vs Saints | 6 - 1 | Christian Athletic League | N/A | Recap |
| 2019-10-12 16:30:33October 12, 2019 | SC Warriors vs Defenders | 3 - 1 | Christian Athletic League | N/A | Recap |
| 2019-10-14 16:30:31October 14, 2019 | Saints vs CCS Warriors | 2 - 4 | Christian Athletic League | N/A | Recap |
| 2019-10-15 16:30:10October 15, 2019 | Maplewood Academy vs CCS Eagles | 0 - 1 | Non-Conference | N/A | Recap |
| 2019-10-15 16:30:57October 15, 2019 | Jaguars vs Metro United | 1 - 1 | Non-Conference | N/A | Recap |
| 2019-10-18 16:00:50October 18, 2019 | St. Francis Christian School vs Jaguars | 6 - 3 | Non-Conference | N/A | Recap |
