| Mon, Nov 30 | Varsity Basketball (A) vs Beavercreek | W 77-41 | 2-0 |
| Tue, Dec 01 | Varsity B White Bowling (A) vs Moeller | W 2618-1735 | 2-0 / Macke - 454, Freed - 410, Costello - 404 |
| | Varsity A Purple Bowling (A) vs Moeller | W 2741-2128 | 1-0 / Stenger - 418, Herbers - 402 |
| | Junior Varsity Bowling (A) vs Moeller | W 1824-1551 | 2-0 / Westendorf - 327 |
| Thu, Dec 03 | Varsity Swimming and Diving (A) vs St. Xavier | 5:00 PM | St. Xavier |
| | Varsity Swimming (A) vs St. Xavier | 5:00 PM | St. Xavier |
| Fri, Dec 04 | Varsity Hockey (A) vs Beavercreek | 6:00 PM | Kettering Rec Center |
| Sat, Dec 05 | Varsity Wrestling (H) vs Elder Duals | 10:00 AM | Elder Wrestling Gym / Round Robin Duals: Elder, Sycamore, Colerain, Legacy Christian, & Graham |
| | Junior Varsity Wrestling (A) vs Taylor | 10:00 AM | Taylor HS / JV Dual Tournament |
| | Varsity Basketball (H) vs Sycamore | 4:30 PM | Elder Memorial Fieldhouse |
| | Freshman Wrestling (H) vs St. X | 6:00 PM | Elder High School / 6pm: Elder vs St. Xavier |
| | Freshman Basketball (H) vs Sycamore | 6:30 PM | Elder Memorial Fieldhouse |
| Sun, Dec 06 | Varsity Hockey (H) vs Alter | 10:00 AM | Northlands |
| Mon, Dec 07 | Junior Varsity Bowling (A) vs Mason | 4:00 PM | Mason Bowl / / |
| | Varsity A Purple Bowling (A) vs Mason | 4:00 PM | Mason Bowl / / |
| | Junior Varsity Basketball (H) vs Sycamore | 5:00 PM | Elder Memorial Fieldhouse |
| Tue, Dec 08 | Varsity Swimming and Diving (A) vs Princeton | 5:00 PM | Princeton High School |
| | Varsity Swimming (A) vs Princeton | 5:00 PM | Princeton High School |
| Wed, Dec 09 | Varsity B White Bowling (H) vs Taylor | 4:00 PM | Western Bowl |
| | Junior Varsity Bowling (H) vs Taylor | 4:00 PM | Western Bowl |
| | Varsity Hockey (H) vs Sycamore | 7:00 PM | Northlands |
| Thu, Dec 10 | Junior Varsity Wrestling (A) vs Fairfield | 5:00 PM | Fairfield High School / Dual: Fairfield JV |
| | Freshman Wrestling (A) vs Fairfield | 5:00 PM | Fairfield High School |
| | Varsity Wrestling (A) vs Fairfield Dual | 7:00 PM | Fairfield High School / Dual: Fairfield |
| Fri, Dec 11 | Varsity A Purple Bowling (H) vs St. Xavier | 7:00 PM | Western Bowl |
| | Varsity B White Bowling (H) vs St. Xavier | 7:00 PM | Western Bowl |
| | Junior Varsity Bowling (H) vs St. Xavier | 7:00 PM | Western Bowl |
| Sat, Dec 12 | Varsity Wrestling (A) vs Ashland Dual Tournament | 10:00 AM | Ashland High School |
| | Junior Varsity Wrestling (A) vs Lakota East JV | 10:00 AM | Lakota East High School / JV Quad: Lakota East, Milford, Loveland |
| | Junior Varsity Basketball (A) vs Summit Country Day School | 5:30 PM | Summit Country Day |
| | Varsity Hockey (A) vs Troy | 5:30 PM | Hobart Arena |
| | Varsity Basketball (A) vs Summit Country Day School | 7:00 PM | Summit Country Day |
| | Varsity Swimming (A) vs Lebanon | TBA | TBA |
| | Varsity Swimming and Diving (A) vs Lebanon | TBA | TBA |
| Sun, Dec 13 | Varsity B White Bowling (H) competes in the Holiday Classic Tournament. | 8:30 AM | Western Bowl / Doors open at 8:30, practice starts at 9:30 |
| | Varsity A Purple Bowling (H) competes in the Holiday Classic Tournament. | 8:30 AM | Western Bowl / Doors open at 8:30, practice starts at 9:30 |
| | Varsity Hockey (A) vs Mason H.S. | 3:00 PM | South Metro |
| Tue, Dec 15 | Junior Varsity Bowling (H) vs Fenwick | 4:15 PM | Western Bowl |
| | Varsity B White Bowling (H) vs Fenwick | 4:15 PM | Western Bowl |
| Fri, Dec 18 | Varsity Hockey (A) vs Moeller H.S | 4:00 PM | Northlands |