| October |
| % | 16 | 6:00PM | SWIC | @ | Kaskaskia | 0-0 | |
| % | 29 | 8:00PM | Kaskaskia | @ | Lewis-Clark State College | 0-0 | |
| | 31 | 7:30PM | TBA | @ | Wabash Valley | 92-102 | |
| | New Creations Prep | |
| | | 8:00PM | Mid-Continent College | @ | Logan | 57-114 | |
| November |
| | 1 | 3:00PM | Dyerburg State CC | @ | Logan | 49-116 | |
| | | 3:00PM | Lewis & Clark CC | @ | Rend Lake | 76-62 | |
| | 3 | 7:00PM | Brehm Prep | @ | Rend Lake | 58-74 | |
| | 4 | 7:30PM | Lindsey Wilson | @ | SIC | 42-72 | |
| | | 7:30PM | Wabash Valley | @ | Volunteer State CC | 94-92 | |
| | 5 | 7:00PM | Rend Lake | @ | Lincoln College | 89-81 | |
| | 8 | 3:00PM | Rend Lake | @ | Danville Area CC | 86-84 | |
| | | 3:00PM | Kaskaskia | vs. | State Fair CC | 75-57 | |
| | | 7:30PM | Three Rivers CC | @ | SIC | 59-75 | |
| | | 7:30PM | Kennedy-King College | @ | Wabash Valley | 76-83 | |
| | | 8:00PM | Logan | @ | Mineral Area College | 83-72 | |
| | 11 | 7:30PM | State Fair CC | @ | SIC | 52-60 | |
| | | 7:30PM | TBA | @ | Wabash Valley | 64-87 | |
| | BREHM Prep | |
| | | 7:30PM | Vincennes University | @ | Kaskaskia | 85-75 | (OT) |
| | 12 | 7:00PM | St. Louis CC- Meramec | @ | Rend Lake | 60-68 | |
| | | 8:00PM | Logan | @ | Mid-Continent College | 83-100 | |
| | 13 | 7:30PM | Wabash Valley | @ | Danville Area CC | 78-75 | |
| | 14 | 4:00PM | SIC | vs. | Allegheny College | 87-64 | |
| | 15 | 3:00PM | Logan | @ | St. Louis CC- Meramec | 70-75 | |
| | | 3:00PM | Danville Area CC | @ | Rend Lake | 69-72 | |
| | | 4:00PM | SIC | vs. | Simmons College of Kentucky | 58-54 | |
| | | 5:00PM | Mineral Area College | @ | Kaskaskia | 72-67 | |
| | 17 | 7:00PM | Rend Lake | @ | Brehm Prep | 79-75 | |
| | | 7:30PM | Lindsey Wilson | @ | Wabash Valley | 70-97 | |
| | 18 | 7:00PM | Logan | @ | Three Rivers CC | 81-72 | |
| | 19 | 7:00PM | Lincoln College | @ | Rend Lake | 59-72 | |
| | | 7:30PM | West Kentucky Tech | @ | SIC | 45-100 | |
| | 20 | 7:30PM | Danville Area CC | @ | Wabash Valley | 78-89 | |
| | 21 | 3:30PM | SIC | vs. | Moberly Area CC | 81-73 | |
| | | 7:30PM | McKendree University | @ | Kaskaskia | 57-82 | |
| | 22 | 3:00PM | Shawnee CC | @ | Rend Lake | 83-96 | |
| | | 7:30PM | SIC | @ | State Fair CC | 69-65 | |
| | 24 | 7:00PM | Lindenwood University | @ | Rend Lake | 76-84 | |
| | | 7:30PM | Washington State | @ | Kaskaskia | 77-94 | |
| | 25 | 7:30PM | Vincennes University | @ | SIC | 59-82 | |
| December |
| | 1 | 7:30PM | St. Louis CC-Forest Park | @ | Wabash Valley | 80-98 | |
| | 2 | 7:00PM | Logan | @ | Vincennes University | 70-78 | |
| | | 7:00PM | McKendree University | @ | Rend Lake | 65-90 | |
| | | 7:30PM | State Fair CC | @ | Kaskaskia | 62-63 | |
| | 3 | 7:30PM | Rend Lake | @ | Shawnee CC | 81-79 | |
| | 4 | 7:30PM | Georgetown College | @ | SIC | 51-107 | |
| | | 7:30PM | Wabash Valley | @ | Kennedy-King College | 64-75 | |
| | 5 | 7:30PM | Greenville College | @ | Kaskaskia | 48-85 | |
| | | 8:00PM | TBA | @ | Logan | 92-106 | |
| | Mississippi Elite Christsian Academy | |
| | 6 | 2:00PM | SIC | @ | Vincennes University | 72-69 | |
| | | 3:00PM | TBA | @ | Logan | 89-93 | |
| | New Creations Prep School | |
| | 8 | 7:30PM | Brehm Prep | @ | Logan | 56-88 | |
| | | 7:30PM | Simmons College of Kentucky | @ | Wabash Valley | 82-98 | |
| | 12 | 7:30PM | Wabash Valley | @ | Kankakee CC | 84-86 | |
| | 13 | 1:00PM | Wabash Valley | vs. | Parkland College | 85-83 | |
| | 15 | 7:00PM | SIC | @ | West Kentucky Tech | CNCL | |
| January |
| | 3 | 7:30AM | Brehm Prep | @ | SIC | 51-76 | |
| | 5 | 7:00PM | Wabash Valley | @ | St. Louis CC-Forest Park | 100-77 | |
| | | 7:30PM | Vincennes University | @ | Logan | 65-57 | |
| * | 7 | 7:30PM | Logan | @ | Lincoln Trail | 59-76 | |
| * | | 7:30PM | SWIC | @ | Wabash Valley | 83-69 | |
| * | | 7:30PM | Lake Land | @ | SIC | 68-79 | |
| * | | 7:30PM | Rend Lake | @ | Olney Central | 94-96 | (2OT) |
| * | 10 | 3:00PM | Lake Land | @ | Logan | 61-63 | |
| * | | 3:00PM | SIC | @ | Rend Lake | 78-66 | |
| | | 3:00PM | Lincoln Trail | @ | Kaskaskia | 80-82 | |
| * | 14 | 7:30PM | Logan | @ | Rend Lake | 54-58 | |
| * | | 7:30PM | Wabash Valley | @ | Lake Land | 82-91 | |
| * | | 7:30PM | SIC | @ | Kaskaskia | 78-66 | |
| * | 17 | 3:00PM | Olney Central | @ | Logan | 56-87 | |
| * | | 7:30PM | Rend Lake | @ | Wabash Valley | 84-86 | |
| * | | 7:30PM | SWIC | @ | SIC | 74-82 | |
| * | | 7:30PM | Kaskaskia | @ | Lake Land | 78-83 | |
| * | 19 | 7:30PM | Kaskaskia | @ | Logan | 86-96 | |
| * | | 7:30PM | Wabash Valley | @ | Olney Central | 71-77 | |
| * | | 7:30PM | Rend Lake | @ | Lincoln Trail | 64-56 | |
| | | 7:30PM | Kaskaskia | @ | Logan | 86-96 | |
| * | 21 | 7:30PM | Logan | @ | SWIC | 76-85 | |
| * | | 7:30PM | Wabash Valley | @ | SIC | 70-82 | |
| * | | 7:30PM | Kaskaskia | @ | Rend Lake | 87-83 | (OT) |
| * | 24 | 3:30PM | Wabash Valley | @ | Kaskaskia | 91-76 | |
| * | | 7:30PM | SIC | @ | Lincoln Trail | 67-63 | |
| * | 25 | 3:00PM | SWIC | @ | Rend Lake | 66-64 | |
| * | 28 | 7:30PM | Olney Central | @ | SIC | PPD | |
| | Rescheduled 2/9/09 | |
| * | | 7:30PM | SWIC | @ | Kaskaskia | 77-54 | |
| * | 31 | 3:00PM | SIC | @ | Logan | 85-76 | |
| * | | 7:30PM | Lincoln Trail | @ | Wabash Valley | 79-89 | |
| * | | 7:30PM | Rend Lake | @ | Lake Land | 65-72 | |
| * | | 7:30PM | Kaskaskia | @ | Olney Central | 81-84 | |
| February |
| | 2 | 7:30PM | Volunteer State CC | @ | Wabash Valley | 68-107 | |
| | 4 | 6:00PM | Kaskaskia | @ | Vincennes University | 90-76 | |
| * | | 7:30PM | Lincoln Trail | @ | Logan | 51-71 | |
| * | | 7:30PM | Wabash Valley | @ | SWIC | 78-83 | |
| * | | 7:30PM | SIC | @ | Lake Land | 65-75 | |
| * | | 7:30PM | Olney Central | @ | Rend Lake | 80-73 | |
| * | 7 | 7:30PM | Logan | @ | Lake Land | 70-61 | |
| * | | 7:30PM | Rend Lake | @ | SIC | 53-63 | |
| * | | 7:30PM | Kaskaskia | @ | Lincoln Trail | 45-64 | |
| * | 9 | 7:30PM | Olney Central | @ | SIC | 71-90 | |
| | Rescheduled from 1/28/09 | |
| * | | 7:30PM | Logan | @ | Wabash Valley | 110-108 | (2OT) |
| * | 11 | 7:30PM | Rend Lake | @ | Logan | 64-93 | |
| * | | 7:30PM | Lake Land | @ | Wabash Valley | 79-86 | |
| * | | 7:30PM | Kaskaskia | @ | SIC | 62-67 | (OT) |
| * | 14 | 3:00PM | Lake Land | @ | Kaskaskia | 69-76 | |
| * | | 7:30PM | Logan | @ | Olney Central | 83-59 | |
| * | | 7:30PM | SIC | @ | SWIC | 72-79 | |
| * | | 8:00PM | Wabash Valley | @ | Rend Lake | 105-102 | (2OT) |
| * | 16 | 7:30PM | Logan | @ | Kaskaskia | 85-77 | |
| * | | 7:30PM | Olney Central | @ | Wabash Valley | 82-68 | |
| * | | 7:30PM | Lincoln Trail | @ | Rend Lake | 73-74 | |
| * | 18 | 7:30PM | SWIC | @ | Logan | 82-80 | (OT) |
| * | | 7:30PM | SIC | @ | Wabash Valley | 83-91 | |
| * | | 7:30PM | Rend Lake | @ | Kaskaskia | 73-68 | |
| | 21 | 12:00PM | Logan | @ | McKendree University | 84-45 | |
| * | | 3:00PM | Rend Lake | @ | SWIC | 58-83 | |
| * | | 7:30PM | Kaskaskia | @ | Wabash Valley | 84-100 | |
| * | | 7:30PM | Lincoln Trail | @ | SIC | 53-98 | |
| * | 25 | 7:30PM | Wabash Valley | @ | Logan | 64-95 | |
| * | | 7:30PM | SIC | @ | Olney Central | 65-74 | |
| * | 28 | 3:00PM | Lake Land | @ | Rend Lake | 63-65 | |
| * | | 7:30PM | Logan | @ | SIC | 58-72 | |
| * | | 7:30PM | Wabash Valley | @ | Lincoln Trail | 69-61 | |
| March |
| | 5 | 3:00PM | Olney Central | vs. | Wabash Valley | 60-82 | |
| | Region 24/District 11 Tourney @ Rend Lake College | |
| | | 5:00PM | SIC | vs. | Lincoln Trail | 65-70 | (OT) |
| | Region 24 Tournament @ Rend Lake College | |
| | | 7:00PM | Logan | vs. | Lake Land | 76-64 | |
| | Region 24/District 11 Tourney @ Rend Lake College | |
| | 7 | 3:00PM | Lincoln Land CC | @ | Rend Lake | 66-78 | |
| | Region XXIV Quarterfinals | |
| | 8 | 2:00PM | Rend Lake | vs. | Lincoln College | 66-87 | |
| | Region XXIV Semifinals | |