| NCAAB | 03/02 20:00 | - | Bloomfield v Caldwell Cougars | L | 87-70 | |
| NCAAB | 02/29 00:30 | - | Caldwell Cougars v Post | W | 80-63 | |
| NCAAB | 02/24 20:00 | - | Dominican (NY) Chargers v Caldwell Cougars | L | 89-85 | |
| NCAAB | 02/21 00:30 | - | Caldwell Cougars v Jefferson Rams | L | 55-65 | |
| NCAAB | 02/17 18:00 | - | Caldwell Cougars v Holy Family Tigers | W | 95-87 | |
| NCAAB | 02/15 00:30 | - | Caldwell Cougars v Bridgeport Purple Knights | W | 96-84 | |
| NCAAB | 02/13 00:00 | - | Chestnut Hill Griffins v Caldwell Cougars | W | 61-85 | |
| NCAAB | 02/10 20:00 | - | Goldey-Beacom Lightning v Caldwell Cougars | W | 92-101 | |
| NCAAB | 02/07 00:30 | - | Caldwell Cougars v Wilmington Wildcats | L | 81-85 | |
| NCAAB | 02/03 20:00 | - | Caldwell Cougars v Georgian Court Lions | W | 85-70 | |
| NCAAB | 02/01 00:30 | - | Caldwell Cougars v Felician Golden Falcons | L | 61-79 | |
| NCAAB | 01/30 00:30 | - | Caldwell Cougars v Dominican (NY) Chargers | L | 77-92 | |
| NCAAB | 01/24 00:30 | - | Caldwell Cougars v Bloomfield | L | 82-88 | |
| NCAAB | 01/20 20:00 | - | Caldwell Cougars v Chestnut Hill Griffins | W | 74-56 | |
| NCAAB | 01/18 00:30 | - | Post v Caldwell Cougars | W | 80-92 | |
| NCAAB | 01/14 21:00 | - | Jefferson Rams v Caldwell Cougars | W | 75-76 | |
| NCAAB | 01/10 00:30 | - | Caldwell Cougars v Dominican (NY) Chargers | - | Postponed | |
| NCAAB | 01/06 20:00 | - | Wilmington Wildcats v Caldwell Cougars | W | 72-75 | |
| NCAAB | 12/30 20:00 | - | Bridgeport Purple Knights v Caldwell Cougars | L | 96-92 | |
| NCAAB | 12/19 19:00 | - | Caldwell Cougars v Assumption Greyhound | L | 78-81 | |
| NCAAB | 12/14 00:30 | - | Adelphi Panthers v Caldwell Cougars | L | 67-62 | |
| NCAAB | 12/09 18:00 | - | Franklin Pierce Ravens v Caldwell Cougars | L | 85-69 | |
| NCAAB | 12/05 23:00 | - | Queens NY Knights v Caldwell Cougars | L | 88-79 | |
| NCAAB | 11/30 01:00 | - | Felician Golden Falcons v Caldwell Cougars | L | 89-84 | |
| NCAAB | 11/26 19:00 | - | American International Yellow Jackets v Caldwell Cougars | W | 92-100 | |
| NCAAB | 11/22 00:30 | - | St. Thomas Aquinas v Caldwell Cougars | L | 84-76 | |
| NCAAB | 11/15 23:00 | - | Bloomsburg Huskies v Caldwell Cougars | W | 63-85 | |
| NCAAB | 11/11 18:00 | - | Caldwell Cougars v D`Youville Spartans | W | 99-81 | |
| NCAAB | 11/11 00:00 | - | Caldwell Cougars v Mercy Mavericks | W | 114-82 | |
| NCAAB | 03/12 23:30 | 1 | New Haven Chargers v Caldwell Cougars | L | 77-56 |