Schedule:
Please note: All rankings shown are the rankings of the teams on the date that they played one another
| Game | Date | Away Team (Rank) | Away Score | Home Score | Home Team (Rank) | Game Status | Result | Margin |
|---|---|---|---|---|---|---|---|---|
| 1 | 2019-11-05 | Tennessee Tech (328) | 64 | 76 | Western Kentucky (121) | Final | W | 12 |
| 2 | 2019-11-09 | Austin Peay (129) | 75 | 97 | Western Kentucky (121) | Final | W | 22 |
| 3 | 2019-11-15 | Western Kentucky (121) | 79 | 71 | Eastern Kentucky (237) | Final | W | 8 |
| 4 | 2019-11-18 | Campebellsville - Harrodsburg | 66 | 109 | Western Kentucky (121) | Final | W | 43 |
| 5 | 2019-11-22 | Bowling Green (173) | 77 | 75 | Western Kentucky (52) | Final | L | -2 |
| 6 | 2019-11-23 | Illinois State (93) | 69 | 83 | Western Kentucky (52) | Final | W | 14 |
| 7 | 2019-11-25 | Fordham (60) | 64 | 69 | Western Kentucky (52) | Final | W | 5 |
| 8 | 2019-11-29 | Louisville (12) | 71 | 54 | Western Kentucky (82) | Final | L | -17 |
| 9 | 2019-12-03 | Western Kentucky (93) | 74 | 76 | Wright State (136) | Final | L | -2 |
| 10 | 2019-12-07 | Arkansas (10) | 79 | 86 | Western Kentucky (93) | Final/OT | W | 7 |
| 11 | 2019-12-21 | Western Kentucky (90) | 82 | 86 | Rhode Island (68) | Final (OT) | L | -4 |
| 12 | 2019-12-28 | Belmont (133) | 79 | 62 | Western Kentucky (111) | Final | L | -17 |
| 13 | 2020-01-02 | North Texas (151) | 84 | 93 | Western Kentucky (129) | Final | W | 9 |
| 14 | 2020-01-04 | Rice (172) | 61 | 68 | Western Kentucky (129) | Final | W | 7 |
| 15 | 2020-01-09 | Western Kentucky (114) | 62 | 72 | UAB (190) | Final | L | -10 |
| 16 | 2020-01-11 | Western Kentucky (114) | 69 | 53 | Middle Tennessee (318) | Final | W | 16 |
| 17 | 2020-01-16 | Old Dominion (201) | 69 | 71 | Western Kentucky (118) | Final | W | 2 |
| 18 | 2020-01-18 | Charlotte (141) | 63 | 80 | Western Kentucky (118) | Final | W | 17 |
| 19 | 2020-01-22 | Western Kentucky (106) | 64 | 60 | Marshall (184) | Final | W | 4 |
| 20 | 2020-01-25 | Marshall (184) | 84 | 91 | Western Kentucky (106) | Final | W | 7 |
| 21 | 2020-01-30 | Western Kentucky (97) | 65 | 69 | Florida Atlantic (216) | Final | L | -4 |
| 22 | 2020-02-01 | Western Kentucky (97) | 76 | 81 | Florida International (170) | Final | L | -5 |
| 23 | 2020-02-06 | Louisiana Tech (88) | 54 | 65 | Western Kentucky (115) | Final | W | 11 |
| 24 | 2020-02-08 | Southern Miss (279) | 72 | 75 | Western Kentucky (115) | Final | W | 3 |
| 25 | 2020-02-13 | Western Kentucky (104) | 67 | 62 | UTEP (202) | Final | W | 5 |
| 26 | 2020-02-15 | Western Kentucky (104) | 77 | 73 | UTSA (227) | Final (OT) | W | 4 |
| 27 | 2020-02-22 | Charlotte (171) | 72 | 70 | Western Kentucky (104) | Final | L | -2 |
| 28 | 2020-02-27 | Louisiana Tech (96) | 91 | 95 | Western Kentucky (114) | Final (OT) | W | 4 |
| 29 | 2020-03-01 | Western Kentucky (114) | 72 | 78 | North Texas (101) | Final (OT) | L | -6 |
| 30 | 2020-03-07 | Western Kentucky (115) | 91 | 85 | Florida International (167) | Final | W | 6 |
| 31 | 2020-03-12 | UAB (115) | 0 | 0 | Western Kentucky (154) | Cancelled | - | - |