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 | Marymount | 51 | 73 | Longwood (297) | Final | W | 22 |
| 2 | 2019-11-08 | Longwood (297) | 65 | 76 | George Mason (145) | Final | L | -11 |
| 3 | 2019-11-12 | Maryland-Eastern Shore (350) | 55 | 85 | Longwood (297) | Final | W | 30 |
| 4 | 2019-11-14 | St. Francis (NY) (262) | 77 | 86 | Longwood (297) | Final | W | 9 |
| 5 | 2019-11-15 | Randolph College | 53 | 78 | Longwood (297) | Final | W | 25 |
| 6 | 2019-11-18 | Longwood (297) | 48 | 65 | Northern Illinois (157) | Final | L | -17 |
| 7 | 2019-11-26 | Longwood (185) | 58 | 71 | UC-Riverside (147) | Final | L | -13 |
| 8 | 2019-11-29 | Longwood (185) | 51 | 69 | Pacific (171) | Final | L | -18 |
| 9 | 2019-12-04 | Longwood (256) | 41 | 52 | North Carolina A&T (295) | Final | L | -11 |
| 10 | 2019-12-07 | Longwood (256) | 65 | 73 | Morgan State (292) | Final | L | -8 |
| 11 | 2019-12-15 | Longwood (308) | 76 | 72 | Stetson (276) | Final | W | 4 |
| 12 | 2019-12-19 | The Citadel (242) | 102 | 99 | Longwood (290) | Final (3OT) | L | -3 |
| 13 | 2019-12-28 | Longwood (304) | 65 | 78 | George Washington (219) | Final | L | -13 |
| 14 | 2020-01-02 | Longwood (309) | 67 | 91 | Winthrop (223) | Final | L | -24 |
| 15 | 2020-01-04 | South Carolina Upstate (301) | 73 | 56 | Longwood (309) | Final | L | -17 |
| 16 | 2020-01-08 | Longwood (331) | 74 | 56 | Charleston Southern (263) | Final | W | 18 |
| 17 | 2020-01-11 | Longwood (331) | 80 | 83 | Hampton (293) | Final | L | -3 |
| 18 | 2020-01-16 | Presbyterian (318) | 74 | 67 | Longwood (326) | Final | L | -7 |
| 19 | 2020-01-18 | Longwood (326) | 58 | 68 | Campbell (210) | Final | L | -10 |
| 20 | 2020-01-20 | UNC-Asheville (228) | 71 | 66 | Longwood (326) | Final | L | -5 |
| 21 | 2020-01-25 | Longwood (332) | 72 | 62 | High Point (338) | Final | W | 10 |
| 22 | 2020-01-30 | Radford (176) | 67 | 55 | Longwood (331) | Final | L | -12 |
| 23 | 2020-02-01 | Longwood (331) | 84 | 81 | Gardner-Webb (285) | Final (OT) | W | 3 |
| 24 | 2020-02-06 | Charleston Southern (262) | 63 | 71 | Longwood (324) | Final | W | 8 |
| 25 | 2020-02-08 | Winthrop (127) | 70 | 68 | Longwood (324) | Final | L | -2 |
| 26 | 2020-02-10 | Campbell (274) | 56 | 57 | Longwood (324) | Final | W | 1 |
| 27 | 2020-02-13 | Longwood (321) | 71 | 73 | UNC-Asheville (275) | Final | L | -2 |
| 28 | 2020-02-15 | Hampton (300) | 68 | 76 | Longwood (321) | Final | W | 8 |
| 29 | 2020-02-20 | Longwood (315) | 68 | 58 | South Carolina Upstate (305) | Final | W | 10 |
| 30 | 2020-02-22 | High Point (331) | 54 | 57 | Longwood (315) | Final | W | 3 |
| 31 | 2020-02-27 | Longwood (306) | 58 | 55 | Presbyterian (333) | Final | W | 3 |
| 32 | 2020-03-05 | Hampton (303) | 78 | 53 | Longwood (302) | Final | L | -25 |