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 | Holy Cross (214) | 71 | 95 | Maryland (23) | Final | L | -24 |
| 2 | 2019-11-09 | Holy Cross (214) | 83 | 87 | New Hampshire (345) | Final | L | -4 |
| 3 | 2019-11-12 | Fairfield (319) | 68 | 63 | Holy Cross (214) | Final/OT | L | -5 |
| 4 | 2019-11-19 | Northeastern (128) | 101 | 44 | Holy Cross (332) | Final | L | -57 |
| 5 | 2019-11-22 | Harvard (149) | 82 | 74 | Holy Cross (332) | Final | L | -8 |
| 6 | 2019-11-29 | Holy Cross (344) | 69 | 87 | Florida Atlantic (334) | Final | L | -18 |
| 7 | 2019-12-01 | Holy Cross (344) | 69 | 91 | Hofstra (155) | Final | L | -22 |
| 8 | 2019-12-02 | Holy Cross (344) | 81 | 67 | Mercer (232) | Final | W | 14 |
| 9 | 2019-12-07 | Holy Cross (350) | 51 | 68 | San Diego (225) | Final | L | -17 |
| 10 | 2019-12-10 | UMass-Boston | 69 | 66 | Holy Cross (341) | Final (OT) | L | -3 |
| 11 | 2019-12-14 | Holy Cross (341) | 72 | 80 | Canisius (237) | Final | L | -8 |
| 12 | 2019-12-22 | Sacred Heart (206) | 89 | 68 | Holy Cross (350) | Final | L | -21 |
| 13 | 2019-12-29 | Holy Cross (350) | 62 | 74 | Siena (203) | Final | L | -12 |
| 14 | 2020-01-02 | Holy Cross (350) | 70 | 80 | Loyola-Maryland (201) | Final | L | -10 |
| 15 | 2020-01-05 | Navy (198) | 61 | 63 | Holy Cross (350) | Final | W | 2 |
| 16 | 2020-01-08 | Holy Cross (344) | 64 | 82 | Lafayette (194) | Final | L | -18 |
| 17 | 2020-01-11 | Holy Cross (344) | 60 | 75 | Bucknell (231) | Final | L | -15 |
| 18 | 2020-01-15 | Army (321) | 0 | 0 | Holy Cross (346) | Scheduled - 07:05PM ET | - | - |
| 19 | 2020-01-16 | Army (321) | 79 | 67 | Holy Cross (346) | Final | L | -12 |
| 20 | 2020-01-18 | Holy Cross (346) | 69 | 81 | American (251) | Final | L | -12 |
| 21 | 2020-01-22 | Lehigh (303) | 95 | 96 | Holy Cross (346) | Final (OT) | W | 1 |
| 22 | 2020-01-25 | Boston University (196) | 79 | 64 | Holy Cross (346) | Final | L | -15 |
| 23 | 2020-01-29 | Holy Cross (343) | 66 | 81 | Navy (210) | Final | L | -15 |
| 24 | 2020-02-01 | Colgate (113) | 73 | 64 | Holy Cross (343) | Final | L | -9 |
| 25 | 2020-02-05 | Loyola-Maryland (290) | 74 | 60 | Holy Cross (343) | Final | L | -14 |
| 26 | 2020-02-08 | Holy Cross (343) | 68 | 77 | Boston University (191) | Final | L | -9 |
| 27 | 2020-02-12 | Holy Cross (345) | 82 | 89 | Lehigh (327) | Final | L | -7 |
| 28 | 2020-02-15 | Lafayette (181) | 72 | 62 | Holy Cross (345) | Final | L | -10 |
| 29 | 2020-02-17 | Bucknell (261) | 69 | 48 | Holy Cross (345) | Final | L | -21 |
| 30 | 2020-02-23 | Holy Cross (345) | 60 | 90 | Colgate (125) | Final | L | -30 |
| 31 | 2020-02-26 | Holy Cross (346) | 61 | 67 | Army (241) | Final | L | -6 |
| 32 | 2020-02-29 | American (215) | 90 | 47 | Holy Cross (346) | Final | L | -43 |
| 33 | 2020-03-03 | Holy Cross (346) | 62 | 65 | Bucknell (254) | Final | L | -3 |