| Sat, Apr 12 | Boys Varsity Tennis (A) vs Best of the West | TBA | TBD |
| Mon, Apr 14 | Boys Varsity Tennis (H) vs Lebanon | 4:15 PM | Event Cancelled |
| | Boys Junior Varsity Tennis (A) vs Lebanon | 4:15 PM | Lebanon High School |
| Tue, Apr 15 | Boys Junior Varsity Tennis (H) vs Northwest | 4:15 PM | William Henry Harrison High School |
| | Boys Varsity Tennis (A) vs Northwest | 4:15 PM | Northwest High School |
| Thu, Apr 17 | Boys Junior Varsity Tennis (A) vs Talawanda | 4:15 PM | Talawanda High School |
| | Boys Varsity Tennis (H) vs Talawanda | 4:15 PM | William Henry Harrison High School |
| Tue, Apr 22 | Boys Junior Varsity Tennis (A) vs St. Xavier | 4:15 PM | St. Xavier High School |
| | Boys Varsity Tennis (A) vs St. Xavier | 4:15 PM | St. Xavier High School |
| Wed, Apr 23 | Boys Varsity Tennis (A) vs Taylor | 4:15 PM | Taylor High School |
| Thu, Apr 24 | Boys Junior Varsity Tennis (A) vs Taylor | 4:15 PM | Taylor High School |
| Fri, Apr 25 | Boys Varsity Tennis (A) vs Colerain | 4:15 PM | Colerain High School |
| Mon, Apr 28 | Boys Junior Varsity Tennis (H) vs Ross | 4:15 PM | William Henry Harrison High School |
| | Boys Varsity Tennis (A) vs Ross | 4:15 PM | Ross High School |
| Wed, Apr 30 | Boys Varsity Tennis (A) vs Little Miami | 4:15 PM | Little Miami High School |
| | Boys Junior Varsity Tennis (A) vs Little Miami | 4:15 PM | Little Miami High School |
| Thu, May 01 | Boys Varsity Tennis (A) vs Springboro | 5:00 PM | Springboro High School |
| | Boys Junior Varsity Tennis (H) vs Springboro | 5:00 PM | William Henry Harrison High School |
| Fri, May 02 | Boys Varsity Tennis (H) vs Hamilton | 4:15 PM | William Henry Harrison High School |
| Sat, May 03 | Boys Varsity Tennis (A) vs Coaches Classic | TBA | TBD |
| Mon, May 05 | Boys Junior Varsity Tennis (H) vs Covington Catholic | 4:15 PM | William Henry Harrison High School |
| | Boys Varsity Tennis (A) vs Covington Catholic | 4:15 PM | Covington Catholic High School |
| Wed, May 07 | Boys Junior Varsity Tennis (H) vs Anderson | 4:15 PM | William Henry Harrison High School |
| | Boys Varsity Tennis (A) vs Anderson | 4:15 PM | Anderson High School |
| Thu, May 08 | Boys Varsity Tennis (H) vs SWOC | 9:00 AM | William Henry Harrison High School |
| Sat, May 10 | Boys Junior Varsity Tennis (A) vs Coaches Classic | TBA | TBD |
| Tue, May 13 | Boys Varsity Tennis (H) vs Finneytown | 4:15 PM | William Henry Harrison High School |
| Wed, May 14 | Boys Varsity Tennis (A) vs Sectional | 9:00 AM | TBD |