| October |
| % | 19 | | Kaskaskia | @ | SWIC | 0-0 | |
| % | 25 | | Kaskaskia | @ | Lewis & Clark CC | 0-0 | |
| | 31 | | Lincoln Trail | vs. | Columbia State CC | 88-68 | |
| | | 6:00PM | Kaskaskia | @ | Moberly Area CC | 62-85 | |
| November |
| | 1 | | Lincoln Trail | @ | Volunteer State CC | 70-74 | |
| | | 1:00PM | Dyerburg State CC | @ | Logan | 47-70 | |
| | | 1:00PM | Shawnee CC | @ | Rend Lake | 39-89 | |
| | | 2:00PM | SIC | @ | Illinois Central College | 75-89 | |
| | | 4:00PM | Kaskaskia | vs. | Three Rivers CC | 87-76 | |
| | | 5:00PM | Wabash Valley | vs. | Black Hawk College-East | 69-59 | |
| | 2 | 1:00PM | John Wood CC | @ | Logan | 43-72 | |
| | | 3:00PM | Wabash Valley | vs. | Jefferson College | 42-88 | |
| | 4 | 5:30PM | Wabash Valley | @ | Volunteer State CC | 83-90 | |
| | 5 | 5:30PM | Moberly Area CC | @ | Logan | 71-62 | |
| | 8 | | Lincoln Trail | @ | Black Hawk College-East | 76-41 | |
| | | 2:00PM | Rend Lake | @ | Mid-Continent College | 96-40 | |
| | | 5:00PM | SIC | @ | Iowa Western CC | 59-79 | |
| | | 5:30PM | Kennedy-King College | @ | Wabash Valley | 74-96 | |
| | 9 | | Lincoln Trail | vs. | Highland CC-Illinois | 78-66 | |
| | | 1:00PM | SIC | @ | South Suburban | 85-76 | |
| | 10 | 5:30PM | McKendree University | @ | Kaskaskia | 59-63 | |
| | 11 | 5:30PM | Cincinnati State Technical and CC | @ | Wabash Valley | 87-73 | |
| | | 6:00PM | Rend Lake | @ | Dyerburg State CC | 78-69 | |
| | 12 | 6:00PM | Logan | @ | Mid-Continent College | 66-81 | |
| | 13 | 5:30PM | Wabash Valley | @ | Danville Area CC | 69-64 | |
| | 14 | | State Fair CC | @ | Kaskaskia | 69-84 | |
| | | | Lincoln Trail | vs. | Labette | 62-73 | |
| | | 8:00PM | Elgin CC | @ | Logan | 46-93 | |
| | 15 | | Moberly Area CC | @ | Kaskaskia | 74-62 | |
| | | | Lincoln Trail | vs. | Cowley County Community College | 47-66 | |
| | | 1:00PM | Lindsey Wilson | @ | Rend Lake | 45-81 | |
| | | 3:00PM | Bevill State-Sumiton | @ | Logan | 66-62 | |
| | 17 | | Kaskaskia | @ | Lewis & Clark CC | 74-83 | |
| | | 5:30PM | Lindsey Wilson | @ | Wabash Valley | 45-92 | |
| | 18 | | Vincennes University | @ | Lincoln Trail | 67-62 | |
| | 19 | 5:30PM | Rend Lake | @ | Shawnee CC | 84-51 | |
| | | 7:00PM | Mid-Continent College | @ | Logan | 45-77 | |
| | 20 | 5:30PM | Danville Area CC | @ | Wabash Valley | 58-80 | |
| | 21 | 1:00PM | Rend Lake | @ | Kirkwood CC | 69-68 | |
| | 22 | 3:00PM | Rend Lake | vs. | NW Mississippi | 71-69 | |
| | | 5:30PM | St. Louis CC-Forest Park | @ | Wabash Valley | 45-90 | |
| | 25 | | Lincoln Trail | @ | Danville Area CC | 60-71 | |
| | | 5:00PM | Vincennes University | @ | SIC | 68-62 | |
| | | 5:30PM | Wabash Valley | @ | Cincinnati State Technical and CC | 72-84 | |
| | 28 | 2:00PM | Rend Lake | vs. | State Fair CC | 76-73 | |
| | | 6:00PM | SIC | @ | Jefferson College | 45-87 | |
| | 29 | 6:00PM | SIC | @ | Mineral Area College | 59-105 | |
| | | 6:00PM | Rend Lake | @ | Moberly Area CC | 51-72 | |
| | 30 | 12:00PM | SIC | @ | Malcolm X College | 114-47 | |
| December |
| | 2 | 5:00PM | Logan | @ | Vincennes University | 81-91 | |
| | | 5:00PM | Kaskaskia | @ | McKendree University | 58-53 | |
| | | 5:30PM | Cincinnati State Technical and CC | @ | SIC | 86-74 | |
| | 4 | 5:00PM | Wabash Valley | @ | Kennedy-King College | 63-68 | |
| | 6 | | Kaskaskia | vs. | Mineral Area College | 53-52 | |
| | | | State Fair CC | @ | Lincoln Trail | 54-64 | |
| | | | Rend Lake | vs. | Jefferson College | 58-80 | |
| | | 1:00PM | SIC | @ | Vincennes University | 53-85 | |
| | | 5:00PM | Wabash Valley | @ | St. Louis CC-Forest Park | 56-44 | |
| | | 8:00PM | Malcolm X College | @ | Logan | 52-99 | |
| | 7 | 3:00PM | Rock Valley College | @ | Logan | 53-91 | |
| | 8 | | Washington State | @ | Kaskaskia | 73-75 | |
| | 9 | | Lincoln Trail | @ | Shawnee CC | 74-62 | |
| | 10 | 8:00PM | Kaskaskia | @ | Greenville College | CNCL | |
| | 12 | 6:00PM | Wabash Valley | @ | Cumberland College | RAIN | |
| | 13 | | Lincoln Trail | vs. | St. Louis CC-Florissant Valley | 68-43 | |
| | | 2:00PM | Logan | @ | Moberly Area CC | 58-71 | |
| | | 3:00PM | Kaskaskia | @ | State Fair CC | 58-63 | |
| | 15 | | Lincoln Trail | @ | St. Louis CC-Forest Park | 50-53 | |
| | 16 | 5:30PM | Volunteer State CC | @ | Wabash Valley | RAIN | |
| | 17 | 6:00PM | Mineral Area College | @ | Rend Lake | 83-80 | (OT) |
| | 19 | | Kaskaskia | vs. | Parkland College | 59-65 | |
| | | 6:00PM | SIC | @ | Columbia State CC | 55-80 | |
| | 20 | 12:00PM | SIC | vs. | Volunteer State CC | 52-88 | |
| | | 2:00PM | Illinois Central College | @ | Rend Lake | 76-67 | |
| | 30 | | Lincoln Trail | @ | Kishwaukee College | 79-50 | |
| | | 5:30PM | Jefferson College | @ | SIC | 90-46 | |
| January |
| | 2 | 1:00PM | Rend Lake | vs. | North Arkansas College | 74-62 | |
| | Three Rivers Classic vs. North Arkansas | |
| | 3 | 3:00PM | Rend Lake | vs. | Three Rivers CC | 81-88 | |
| | Three Rivers Classic vs. Three Rivers Community College | |
| | | 5:30PM | Dyerburg State CC | @ | SIC | 69-82 | |
| | Game Rescheduled from Dec. 16, 2008 | |
| | 5 | 5:30PM | Vincennes University | @ | Logan | 72-74 | |
| * | 7 | 5:30PM | Logan | @ | Lincoln Trail | 57-62 | |
| * | | 5:30PM | SWIC | @ | Wabash Valley | 48-41 | |
| * | | 5:30PM | Lake Land | @ | SIC | 92-74 | |
| * | | 5:30PM | Rend Lake | @ | Olney Central | 67-43 | |
| * | 10 | 1:00PM | Lake Land | @ | Logan | 76-72 | |
| * | | 1:00PM | SIC | @ | Rend Lake | 65-84 | |
| * | | 1:00PM | Lincoln Trail | @ | Kaskaskia | 69-75 | |
| * | 13 | 6:00PM | SIC | @ | Kaskaskia | | |
| * | 14 | | Lincoln Trail | @ | SWIC | 55-59 | |
| * | | 5:30PM | Logan | @ | Rend Lake | 54-78 | |
| * | | 5:30PM | Wabash Valley | @ | Lake Land | 60-64 | |
| * | | 5:30PM | SIC | @ | Kaskaskia | 61-76 | |
| | 17 | | Lincoln Trail | @ | Vincennes University | 58-70 | |
| * | | 1:00PM | Olney Central | @ | Logan | 51-91 | |
| | | 5:00PM | Kaskaskia | @ | Lake Land | 67-63 | |
| * | | 5:30PM | Rend Lake | @ | Wabash Valley | 80-55 | |
| * | | 5:30PM | SWIC | @ | SIC | 67-72 | |
| * | 19 | 5:30PM | Kaskaskia | @ | Logan | 73-57 | |
| * | | 5:30PM | Wabash Valley | @ | Olney Central | 73-51 | |
| * | | 5:30PM | Rend Lake | @ | Lincoln Trail | 53-50 | |
| * | 21 | | Lincoln Trail | @ | Olney Central | 59-47 | |
| * | | 5:30PM | Logan | @ | SWIC | 42-70 | |
| * | | 5:30PM | Wabash Valley | @ | SIC | 82-91 | |
| * | | 5:30PM | Kaskaskia | @ | Rend Lake | 70-68 | |
| * | 24 | 1:00PM | Wabash Valley | @ | Kaskaskia | 52-56 | |
| * | | 5:30PM | SIC | @ | Lincoln Trail | 46-73 | |
| * | 25 | 1:00PM | SWIC | @ | Rend Lake | 65-72 | |
| * | 28 | 5:30PM | Logan | @ | Wabash Valley | RAIN | |
| * | | 5:30PM | Olney Central | @ | SIC | PPD | |
| | Rescheduled 2/9/09 | |
| * | | 5:30PM | SWIC | @ | Kaskaskia | 68-75 | |
| * | 31 | 1:00PM | SIC | @ | Logan | 65-82 | |
| * | | 5:30PM | Lincoln Trail | @ | Wabash Valley | 69-52 | |
| * | | 5:30PM | Rend Lake | @ | Lake Land | 71-75 | |
| * | | 5:30PM | Kaskaskia | @ | Olney Central | 66-46 | |
| February |
| * | 2 | | Lake Land | @ | Lincoln Trail | 55-67 | |
| | | 5:30PM | Volunteer State CC | @ | Wabash Valley | 101-70 | |
| * | 4 | 5:30PM | Lincoln Trail | @ | Logan | 65-77 | |
| * | | 5:30PM | Wabash Valley | @ | SWIC | 84-77 | (OT) |
| * | | 5:30PM | SIC | @ | Lake Land | 51-76 | |
| * | | 5:30PM | Olney Central | @ | Rend Lake | 70-108 | |
| * | 7 | 5:30PM | Logan | @ | Lake Land | 63-77 | |
| * | | 5:30PM | Rend Lake | @ | SIC | 64-48 | |
| * | | 5:30PM | Kaskaskia | @ | Lincoln Trail | 54-44 | |
| * | 9 | 5:30PM | Olney Central | @ | SIC | 65-74 | |
| | Rescheduled from 1/28/09 | |
| * | | 5:30PM | Logan | @ | Wabash Valley | 74-82 | |
| * | 10 | 5:00PM | Kaskaskia | @ | SIC | 89-94 | |
| * | 11 | | SWIC | @ | Lincoln Trail | 61-54 | |
| * | | 5:30PM | Rend Lake | @ | Logan | 81-45 | |
| * | | 5:30PM | Lake Land | @ | Wabash Valley | 50-45 | |
| * | | 5:30PM | Kaskaskia | @ | SIC | 85-60 | |
| * | 14 | 1:00PM | Lake Land | @ | Kaskaskia | 64-78 | |
| * | | 4:30PM | SIC | @ | SWIC | 53-84 | |
| * | | 5:30PM | Logan | @ | Olney Central | 76-64 | |
| * | | 5:30PM | Wabash Valley | @ | Rend Lake | 66-82 | |
| * | 16 | 5:30PM | Logan | @ | Kaskaskia | 52-61 | |
| * | | 5:30PM | Olney Central | @ | Wabash Valley | 53-80 | |
| * | | 5:30PM | Lincoln Trail | @ | Rend Lake | 63-55 | |
| * | 18 | | Olney Central | @ | Lincoln Trail | 49-63 | |
| * | | 5:30PM | SWIC | @ | Logan | 64-59 | |
| * | | 5:30PM | SIC | @ | Wabash Valley | 102-109 | (2OT) |
| * | | 5:30PM | Rend Lake | @ | Kaskaskia | 74-82 | |
| * | 20 | | Olney Central | @ | Kaskaskia | 65-101 | |
| * | 21 | 1:00PM | Rend Lake | @ | SWIC | 57-43 | |
| * | | 5:30PM | Kaskaskia | @ | Wabash Valley | 73-70 | |
| * | | 5:30PM | Lincoln Trail | @ | SIC | 94-61 | |
| * | 25 | | Lincoln Trail | @ | Lake Land | 52-59 | |
| * | | 5:30PM | Wabash Valley | @ | Logan | 62-58 | |
| * | | 5:30PM | SIC | @ | Olney Central | 92-72 | |
| * | | 5:30PM | Kaskaskia | @ | SWIC | 81-67 | |
| * | 28 | 1:00PM | Lake Land | @ | Rend Lake | 70-91 | |
| * | | 1:00PM | Olney Central | @ | Kaskaskia | 65-101 | |
| * | | 5:30PM | Logan | @ | SIC | 83-72 | |
| * | | 5:30PM | Wabash Valley | @ | Lincoln Trail | 59-75 | |
| March |
| | 3 | 5:30PM | Wabash Valley | @ | Lincoln Trail | 49-59 | |
| | Region 24 Tournament | |
| | | 7:00PM | Olney Central | @ | Kaskaskia | 41-72 | |
| | Region 24 Tournament | |
| | | 7:00PM | SIC | vs. | Rend Lake | 60-83 | |
| | Region 24 Tournament | |
| | | 7:00PM | Logan | @ | SWIC | 62-56 | |
| | Region 24 Tournament | |
| | 6 | 6:00PM | Lincoln Trail | vs. | Kaskaskia | 64-66 | |
| | Region 24 Semi-finals | |
| | | 8:00PM | Rend Lake | @ | Logan | 74-59 | |
| | Region 24 Semifinals | |
| | 7 | 8:00PM | Rend Lake | vs. | Kaskaskia | 69-74 | |
| | Region 24 Championship Finals | |