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 | 2018-11-06 | Western Illinois (266) | 67 | 78 | Creighton (26) | Final | L | -11 |
| 2 | 2018-11-10 | North Park | 56 | 84 | Western Illinois (266) | Final | W | 28 |
| 3 | 2018-11-14 | Dominican (IL) | 56 | 95 | Western Illinois (242) | Final | W | 39 |
| 4 | 2018-11-17 | Western Illinois (242) | 66 | 68 | Eastern Illinois (321) | Final/OT | L | -2 |
| 5 | 2018-11-21 | Western Illinois (286) | 90 | 92 | Tennessee-Martin (305) | Final | L | -2 |
| 6 | 2018-11-24 | Western Illinois (286) | 49 | 73 | Nebraska (11) | Final | L | -24 |
| 7 | 2018-11-28 | SIU-Edwardsville (289) | 58 | 83 | Western Illinois (298) | Final | W | 25 |
| 8 | 2018-12-01 | Western Illinois (298) | 70 | 63 | Southeast Missouri State (238) | Final | W | 7 |
| 9 | 2018-12-05 | Western Illinois (227) | 64 | 68 | Stetson (344) | Final | L | -4 |
| 10 | 2018-12-08 | Eastern Illinois (280) | 74 | 67 | Western Illinois (227) | Final | L | -7 |
| 11 | 2018-12-15 | Western Illinois (296) | 68 | 82 | IUPUI (127) | Final | L | -14 |
| 12 | 2018-12-17 | Western Illinois (296) | 76 | 91 | Northern Illinois (212) | Final | L | -15 |
| 13 | 2018-12-20 | Chicago State (331) | 52 | 81 | Western Illinois (298) | Final | W | 29 |
| 14 | 2018-12-28 | South Dakota State (151) | 100 | 58 | Western Illinois (297) | Final | L | -42 |
| 15 | 2018-12-30 | Denver (288) | 60 | 78 | Western Illinois (297) | Final | W | 18 |
| 16 | 2019-01-05 | Western Illinois (287) | 63 | 82 | Oral Roberts (298) | Final | L | -19 |
| 17 | 2019-01-10 | Western Illinois (306) | 69 | 85 | North Dakota State (224) | Final | L | -16 |
| 18 | 2019-01-12 | Western Illinois (306) | 65 | 71 | North Dakota (292) | Final | L | -6 |
| 19 | 2019-01-17 | Nebraska-Omaha (193) | 80 | 71 | Western Illinois (321) | Final | L | -9 |
| 20 | 2019-01-19 | Purdue Fort Wayne (169) | 58 | 87 | Western Illinois (321) | Final | W | 29 |
| 21 | 2019-01-26 | Western Illinois (313) | 65 | 59 | South Dakota (255) | Final | W | 6 |
| 22 | 2019-01-31 | North Dakota (301) | 0 | 0 | Western Illinois (296) | Postponed | – | – |
| 23 | 2019-02-01 | North Dakota (301) | 74 | 73 | Western Illinois (296) | Final | L | -1 |
| 24 | 2019-02-02 | North Dakota State (223) | 78 | 76 | Western Illinois (296) | Final | L | -2 |
| 25 | 2019-02-07 | Western Illinois (311) | 64 | 79 | Purdue Fort Wayne (171) | Final | L | -15 |
| 26 | 2019-02-16 | South Dakota (278) | 80 | 67 | Western Illinois (314) | Final | L | -13 |
| 27 | 2019-02-20 | Western Illinois (320) | 63 | 77 | Nebraska-Omaha (155) | Final | L | -14 |
| 28 | 2019-02-23 | Oral Roberts (294) | 66 | 75 | Western Illinois (320) | Final | W | 9 |
| 29 | 2019-02-28 | Western Illinois (314) | 46 | 74 | Denver (327) | Final | L | -28 |
| 30 | 2019-03-02 | Western Illinois (314) | 66 | 86 | South Dakota State (102) | Final | L | -20 |
| 31 | 2019-03-09 | Western Illinois (324) | 79 | 76 | South Dakota State (105) | Final | W | 3 |
| 32 | 2019-03-11 | Western Illinois (324) | 73 | 76 | North Dakota State (210) | Final | L | -3 |