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| DATE | OPPONENT | LOCATION | DHS | OPP |
| Dec. 17 | Estelline @ 6:00 p.m. | Estelline | ||
| Dec. 18 | Clark-Willow Lake | Willow Lake | ||
| Dec. 20 | Sioux Valley (Parent's Night / Double Header @ 5:30 p.m.) | White | ||
| Dec. 28 | Swiftel Classic (Deubrook vs. Pipestone, MN @ 8:00 p.m.) | Brookings Swiftel Center | ||
| Dec. 31 | Entringer Classic (Deubrook vs Dell Rapids Public @ 6:15 p.m.) | Brookings High School Auxiliary Gym | ||
| Jan. 4 | DeSmet | White | ||
| Jan. 14 | Elkton / Lake Benton | White | ||
| Jan. 15 | Redfield Classic (TBD) | Redfield | ||
| Jan. 18 | DVC Tournament (Deubrook vs. ) | TBD | ||
| Jan. 21 | DVC Tournament (Deubrook vs ) | TBD | ||
| Jan. 22 | DVC Tournament (Deubrook vs.) | Colman | ||
| Jan. 27 | Lake Preston | White | ||
| Jan. 29 | Castlewood | Castlewood | ||
| Feb. 1 | Deuel | Clear Lake | ||
| Feb. 3 | Dell Rapids St. Mary's @ 6:15 pm | Dell Rapids | ||
| Feb. 8 | Hamlin (Double Header @ 5:00 pm) | Hamlin | ||
| Feb. 10 | Oldham/Ramona/Rutland | TBD | ||
| Feb. 12 | Schoolers Classic (TBA) | Sioux Falls - Elmen Center | ||
| Feb. 14 | Arlington | Toronto | ||
| Feb. 25 | Colman-Egan | Colman | ||
| Mar. 1 | District 4A Tournament (7:00 p.m.) | TBD | ||
| Mar. 4 | District 4A Championship (TBA.) | Swiftel Center-Brookings | ||
| Mar. 8 | Region 2A Championship Game (TBA.) | Swiftel Center Brookings |
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| Mar. 17-19 | State A Boys Basketball Tournament | Rapid City |
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All game times are 6:30 pm unless noted otherwise.
*Denotes Dakota Valley Conference Games
|
| DATE | OPPONENT | LOCATION | DHS | OPP |
| Dec. 11 | Estelline *Parents Nights | Toronto | 43 | 17 |
| Dec. 15 | Hamlin | Toronto | 51 | 38 |
| Dec. 18 | DeSmet | DeSmet | 47 | 29 |
| Dec. 19 | Clark-Willow Lake | Toronto | ||
| JV Team | 29 | 24 | ||
| C Team | 37 | 29 | ||
| Dec. 21 | Sioux Valley | Volga | ||
| JV | 45 | 36 | ||
| C | 29 | 21 | ||
| Dec. 30 | Estelline Tourney | Estelline | ||
| Deubrook JV vs. DeSmet | 36 | 15 | ||
| Deubrook JV vs. Arlington | 51 | 52 | ||
| Deubrook C vs. DeSmet | 71 | 31 | ||
| Deubrook C vs. Estelline | 42 | 33 | ||
| Jan. 15 | Lake Preston | Lake Preston | ||
| JV | 53 | 20 | ||
| C | 51 | 10 | ||
| Jan. 30 | Castlewood | Toronto | 32 | 28 |
| Feb. 1 | Deuel | Toronto | ||
| JV | 39 | 33 | ||
| C | 36 | 31 | ||
| Feb. 4 | Arlington | Arlington | 51 | 57 |
| Feb. 11 | Oldham-Ramona-Rutland | White | 55 | 32 |
| Feb. 15 | Dell Rapids St. Mary | White | 49 | 19 |
| Feb. 19 | Colman-Egan | White | 46 | 28 |
| Feb. 20 | Mitchell Christian | Mitchell | 57 | 35 |
| Feb. 22 | Elkton (Rescheduled from Jan. 8th) | Elkton | ||
| JV | 47 | 37 | ||
| C | 24 | 27 |
| DATE | OPPONENT | Games & Times | LOCATION |
| Dec. 11 | Estelline | 3:45: 7th & 4:30: 8th | Toronto |
| Dec. 15 | Hamlin | 3:45: 7th & 4:30: 8th | Toronto |
| Dec. 18 | DeSmet | TBD | DeSmet |
| Jan. 9 | 7th & 8th DeSmet Tourney | TBD | DeSmet |
| Jan. 15 | Lake Preston | 4:00: 7th & 5:00: 8th | Lake Benton, MN |
| Jan. 16 | 8th Jamboree | 9:00 am | Clear Lake |
| Jan. 30 | Castlewood | 3:45: 7th & 4:30: 8th | Toronto |
| Feb. 1 | Deuel | 3:00: 7th & 4:00: 8th | Toronto |
| Feb. 4 | Arlington | TBD | Arlington |
| Feb. 6 | Estelline 7th / 8th Tourney | 9:00 am | Estelline |
| Feb. 11 | Oldham-Ramona-Rutland 1 combined | 5:00 | White |
| Feb. 15 | Dell Rapids St. Mary | 3:45: 7th & 4:30: 8th | White |
| Feb. 22 | Elkton-Lake Benton | 4:00: 7th & 5:00: 8th | Lake Benton |