| Holy Cross Coll. Games/Schedule |
| Regular Season |
| Oct. 27, 2018 | Day 13 | Mich.-Dearborn - Holy Cross Coll. | 53-70  |
| Oct. 30, 2018 | Day 16 | Holy Cross Coll. - Great Lakes Chr. | 77-56 |
| Nov. 6, 2018 | Day 23 | Holy Cross Coll. - Grace Coll. | 56-66  |
| Nov. 8, 2018 | Day 25 | Andrews - Holy Cross Coll. | 51-63 |
| Nov. 14, 2018 | Day 31 | Holy Cross Coll. - St.Xavier | 73-85 |
| Nov. 17, 2018 | Day 34 | Holy Cross Coll. - Judson | 58-53 |
| Nov. 20, 2018 | Day 37 | IU S.Bend - Holy Cross Coll. | 79-84 |
| Nov. 24, 2018 | Day 40 | IU Northwest - Holy Cross Coll. | 74-87 |
| Nov. 28, 2018 | Day 44 | Robert Morris - Holy Cross Coll. | 79-76 |
| Dec. 1, 2018 | Day 47 | St.Francis, IL - Holy Cross Coll. | 77-66 |
| Dec. 6, 2018 | Day 52 | Holy Cross Coll. - Andrews | 72-36 |
| Dec. 8, 2018 | Day 54 | Holy Cross Coll. - Trinity Intern. | 65-46 |
| Dec. 13, 2018 | Day 59 | Great Lakes Chr. - Holy Cross Coll. | 70-63 |
| Dec. 15, 2018 | Day 61 | Calumet - Holy Cross Coll. | 67-66 |
| Dec. 19, 2018 | Day 65 | Holy Cross Coll. - East-West | 100-60 |
| Dec. 21, 2018 | Day 67 | IU East - Holy Cross Coll. | 73-69 |
| Dec. 30, 2018 | Day 72 | Goshen - Holy Cross Coll. | 71-64 |
| Jan. 5, 2019 | Day 78 | Olivet Nazarene - Holy Cross Coll. | 73-55 |
| Jan. 9, 2019 | Day 82 | Holy Cross Coll. - Roosevelt | 79-75 |
| Jan. 12, 2019 | Day 85 | St.Ambrose - Holy Cross Coll. | 75-80 |
| Jan. 16, 2019 | Day 89 | Holy Cross Coll. - Governors St. | 73-54 |
| Jan. 19, 2019 | Day 92 | Holy Cross Coll. - Cardinal Stritch | 62-59 |
| Jan. 23, 2019 | Day 96 | Trinity Christian - Holy Cross Coll. | 58-69 |
| Jan. 26, 2019 | Day 99 | St.Xavier - Holy Cross Coll. | 68-66 |
| Feb. 2, 2019 | Day 106 | Holy Cross Coll. - IU S.Bend | 56-49 |
| Feb. 4, 2019 | Day 107 | Judson - Holy Cross Coll. | 68-73 |
| Feb. 6, 2019 | Day 109 | Holy Cross Coll. - Robert Morris | 78-61 |
| Feb. 9, 2019 | Day 112 | Holy Cross Coll. - St.Francis, IL | 77-76 |
| Feb. 13, 2019 | Day 116 | Trinity Intern. - Holy Cross Coll. | 69-79 |
| Feb. 16, 2019 | Day 119 | Holy Cross Coll. - Calumet | 88-71 |
| Feb. 19, 2019 | Day 121 | Holy Cross Coll. - Cardinal Stritch | 82-68 |
| Feb. 21, 2019 | Day 123 | Holy Cross Coll. - Governors St. | 64-70 |
