| 1 | Mon Nov 4 | at Illinois | L67-112 | 0-1 | .000 | - | B1G+ | State Farm Center · Champaign, IL |
| 2 | Wed Nov 6 | vs TBD | W97-61 | 1-1 | .500 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 3 | Sun Nov 10 | at #17Indiana | L55-90 | 1-2 | .333 | - | B1G+ | Simon Skjodt Assembly Hall · Bloomington, IN |
| 4 | Fri Nov 15 | at Northwestern | L58-67 (OT) | 1-3 | .250 | - | Peacock | Welsh-Ryan Arena · Evanston, IL |
| 5 | Tue Nov 19 | at DePaul | L69-78 | 1-4 | .200 | - | FS2 | Wintrust Arena · Chicago, IL |
| 6 | Sun Nov 24 | at Valparaiso | L53-81 | 1-5 | .167 | - | ESPN+ | Athletics-Recreation Center · Valparaiso, IN |
| 7 | Fri Nov 29 | vs N Illinois | W72-59 | 2-5 | .286 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 8 | Tue Dec 3 | at Butler | L58-73 | 2-6 | .250 | - | FS2 | Hinkle Fieldhouse · Indianapolis, IN |
| 9 | Fri Dec 6 | vsTBD | W87-57 | 3-6 | .333 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 10 | Sat Dec 14 | at E Kentucky | L66-81 | 3-7 | .300 | - | ESPN+ | McBrayer Arena · Richmond, KY |
| 11 | Thu Dec 19 | at SE Missouri St | L72-79 | 3-8 | .273 | - | ESPN+ | Show Me Center · Cape Girardeau, MO |
| 12 | Sat Dec 21 | at Little Rock | PPD | 9-19 | .321 | - | | Jack Stephens Center · Little Rock, AR |
| 13 | Sat Dec 28 | vsTBD | W99-55 | 4-8 | .333 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 14 | Thu Jan 2 | vs Lindenwood | W78-74 (OT) | 5-8 | .385 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 15 | Sat Jan 4 | vs W Illinois | L67-75 | 5-9 | .357 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 16 | Tue Jan 7 | vs SIUE | L57-60 | 5-10 | .333 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 17 | Thu Jan 9 | vs Tennessee Tech | L64-69 | 5-11 | .313 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 18 | Thu Jan 16 | at UT Martin | L63-68 | 5-12 | .294 | - | ESPN+ | Kathleen and Tom Elam Center · Martin, TN |
| 19 | Sat Jan 18 | at Tennessee St | L65-84 | 5-13 | .278 | - | ESPN+ | Gentry Center · Nashville, TN |
| 20 | Thu Jan 23 | vs Morehead St | L66-73 | 5-14 | .263 | - | ESPNU | Lantz Arena · Charleston, IL |
| 21 | Sat Jan 25 | vs So Indiana | L60-64 | 5-15 | .250 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 22 | Mon Jan 27 | atLittle Rock | W56-54 | 6-15 | .286 | - | ESPN+ | Jack Stephens Center · Little Rock, AR |
| 23 | Thu Jan 30 | atW Illinois | W71-59 | 7-15 | .318 | - | ESPN+ | LeRoy A. Ufkes Court at Western Hall · Macomb, IL |
| 24 | Sat Feb 1 | atLindenwood | W76-70 | 8-15 | .348 | - | ESPN+ | placeholder · sf, ca |
| 25 | Tue Feb 4 | atSIUE | L41-66 | 8-16 | .333 | - | ESPN+ | First Community Arena at the Vadalabene Center · Edwardsville, IL |
| 26 | Sat Feb 8 | atTennessee Tech | L54-59 | 8-17 | .320 | - | ESPN+ | Hooper Eblen Center · Cookeville, TN |
| 27 | Thu Feb 13 | vsTennessee St | L49-66 | 8-18 | .308 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 28 | Sat Feb 15 | vsUT Martin | L68-72 | 8-19 | .296 | - | ESPN+ | Lantz Arena · Charleston, IL |
| 29 | Thu Feb 20 | atSo Indiana | W63-54 | 9-19 | .321 | - | ESPN+ | Screaming Eagles Arena · Evansville, IN |
