- % Scrimmage Event
- Event times are (CST)
| October |
| | 29 | 4:00PM | University of Winnipeg | @ | Jamestown | 57-76 | |
| | final score | |
| November |
| | 4 | 7:30PM | Dordt College | @ | Jamestown | 79-64 | |
| | 5 | 4:00PM | Northwestern College | @ | Jamestown | 69-66 | |
| | 8 | 7:00PM | Jamestown | @ | University of Minnesota-Crookston | 68-70 | |
| | 11 | 7:00PM | Doane College | @ | Jamestown | 78-80 | (OT) |
| | 12 | 3:00PM | Briercrest College | @ | Jamestown | 34-106 | |
| | 18 | 6:00PM | Jamestown | vs. | College of Saint Scholastica | 78-45 | |
| | American Family Classic @ St. Cloud, MN | |
| | 22 | 7:30PM | Jamestown | @ | University of Minnesota-Morris | 80-64 | |
| | 25 | 6:00PM | Jamestown | vs. | William Penn University | 72-69 | |
| | Statesman Classic @ Oskaloosa, Iowa | |
| | 26 | 2:00PM | Jamestown | vs. | Presentation College | 80-40 | |
| | Statesman Classic @ Oskaloosa, Iowa | |
| December |
| | 4 | 4:00PM | Oglala Lakota College | @ | Jamestown | 46-115 | |
| | Final | |
| | 6 | 7:30PM | Presentation College | @ | Jamestown | 40-86 | |
| | 7 | 7:30PM | Trinity Bible College | @ | Jamestown | 60-87 | |
| | 17 | 6:00PM | Jamestown | @ | Southeastern College | 62-58 | |
| | @ Lakeland, FL, Southeastern was ranked 15th, Jamestown 13th | |
| | 19 | 6:00PM | Jamestown | @ | Warner Southern | 60-56 | |
| | @ Lake Wales, FL, Warner was ranked 18th, Jamestown 13th | |
| | 29 | 3:00PM | Jamestown | vs. | Morningside College | 59-68 | |
| | @ Briar Cliff Tournament, Morningside was ranked # 22 in Dec. 12 poll | |
| | 30 | 7:30PM | Jamestown | @ | Briar Cliff University | 72-65 | (OT) |
| | @ Briar Cliff Tournament; Briar Cliff ranked # 29, Jamestown 13 | |
| January |
| | 3 | 7:30PM | Dakota State | @ | Jamestown | 51-58 | |
| | 6 | 8:30PM | Jamestown | @ | South Dakota School of Mines & Tech. | 77-70 | |
| | 7 | 5:00PM | Jamestown | @ | Oglala Lakota College | 107-65 | |
| | 14 | 6:00PM | Jamestown | @ | Dakota State | 71-61 | |
| | Jamestown is No. 10 in the latest NAIA Division II Men's Basketball national poll, while DSU receives votes. | |
| | 21 | 8:00PM | Jamestown | vs. | Dickinson State | 60-55 | |
| | DAC Tournament @ Valley City, ND | |
| | 22 | 6:00PM | Jamestown | vs. | Mayville State | 66-53 | |
| | DAC Tournament, Championship | |
| * | 28 | 6:00PM | Jamestown | @ | Mayville State | 66-51 | |
| February |
| * | 1 | 7:30PM | Valley City | @ | Jamestown | 86-83 | (OT) |
| * | 4 | 7:30PM | Dickinson State | @ | Jamestown | 67-81 | |
| | Senior Day | |
| * | 8 | 7:30PM | Jamestown | @ | Valley City | 80-77 | (OT) |
| * | 15 | 7:30PM | Mayville State | @ | Jamestown | 55-72 | |
| * | 18 | 7:00PM | Jamestown | @ | Dickinson State | 64-53 | |
| | 6 pm MST, 7 pm CST | |
| | 25 | 7:00PM | Jamestown | vs. | Dickinson State | 71-70 | |
| | A.I.I. Tournament @ Madison, SD | |
| | 26 | 6:00PM | Jamestown | vs. | Dakota State | 71-80 | |
| | Championship - A.I.I. Tournament @ Madison, SD | |
| March |
| | 8 | 10:15AM | Jamestown | vs. | University of Saint Francis | 63-64 | |
| | NAIA National Tournament @ Point Lookout, MO | |
% Exhibition/Scrimmage Event
Event times are ()
