| October |
| | 30 | 8:00PM | Indiana - South Bend | @ | Purdue North Central | 2-0 | |
| | Forfeit |
| | 31 | 3:00PM | Silver Lake College | @ | Calumet St. Joseph | 71-84 | |
| | | 7:00PM | Trinity International | @ | McKendree University | 73-83 | |
| | Listen Live |
| November |
| | 4 | 7:00PM | Andrews University | @ | Purdue North Central | 2-0 | |
| | Forfeit |
| | | 7:00PM | East-West University | @ | Trinity International | 86-100 | |
| % | | 7:00PM | Cardinal Stritch | @ | Wisconsin-Milwaukee | 72-74 | |
| | | 7:30PM | Calumet St. Joseph | @ | St. Francis | 84-94 | |
| | 6 | 6:00PM | Iowa Wesleyan College | vs. | Judson | 74-85 | |
| | Mt. Mercy Classic (Cedar Rapids, IA) |
| | | 7:00PM | Indiana Wesleyan University | @ | Purdue Calumet | 90-55 | |
| | Tip-Off Classic |
| | | 8:00PM | Trinity International | @ | Mount Mercy College | 73-91 | |
| | Mt. Mercy (Iowa) Classic |
| | 7 | 1:00PM | Malone College | @ | Calumet St. Joseph | 85-76 | |
| | | 2:00PM | Trinity International | @ | Iowa Wesleyan College | 84-98 | |
| | Mt. Mercy (Iowa) Classic |
| | | 3:00PM | Trinity Christian | @ | Viterbo University | 58-78 | |
| | | 4:00PM | Judson | @ | Mount Mercy College | 92-106 | |
| | Mt. Mercy Classic (Cedar Rapids, IA) |
| | | 4:00PM | Indiana University Northwest | @ | Purdue Calumet | 89-88 | |
| | Tip-Off Classic |
| | 10 | 7:00PM | Trinity International | @ | Clarke College | 97-86 | |
| | Live Stats / Listen Live |
| | | 7:00PM | Saint Xavier | @ | Calumet St. Joseph | 81-65 | |
| | | 7:30PM | Judson | @ | Ashford University | 75-80 | |
| | 13 | 6:00PM | Purdue North Central | vs. | Indiana University Southeast | 65-95 | |
| | IU/PU Challenge, hosted by IU-East |
| | | 7:00PM | Trinity International | @ | Huntington College | 69-92 | |
| | Huntington University Tournament |
| | | 8:00PM | Judson | @ | Bethel College | 92-121 | |
| | Bethel College Tournament (Mishawaka, IN) - Bethel is #3 in NAIA National Poll. |
| | | 8:00PM | Purdue Calumet | @ | Indiana University East | 84-101 | |
| | IU-PU Challenge |
| | | 8:00PM | Kuyper College | @ | Trinity Christian | 68-82 | |
| | Mitchell Memorial Classic |
| | | 8:00PM | Cardinal Stritch | @ | MidAmerica Nazarene University | 68-70 | |
| | MidAmerica Nazarene Classic |
| | 14 | | Trinity International | @ | William Penn University | 83-94 | |
| | Huntington University Tournament |
| | | 1:00PM | Judson | vs. | Marian College | 70-82 | |
| | Bethel College Tournament (Mishawaka, IN) |
| | | 2:00PM | Purdue Calumet | vs. | Indiana University Southeast | 95-106 | |
| | IU-PU Challenge |
| | | 2:30PM | Calumet St. Joseph | @ | Cincinnati Christian University | 90-103 | |
| | Listen Live on RSN |
| | | 3:00PM | Purdue North Central | @ | Indiana University East | 74-80 | |
| | IU/PU Challenge hosted by IU-East |
| | | 3:00PM | Cedarville University | @ | Trinity Christian | 98-76 | |
| | Mitchell Memorial Classic |
| | | 6:00PM | Cardinal Stritch | vs. | Benedictine College | 90-81 | |
| | MidAmerica Nazarene Classic |
| | 17 | 5:30PM | Great Lakes Christian College | @ | Trinity Christian | 72-115 | |
| | | 7:00PM | Judson | @ | Indiana University Northwest | 103-110 | |
| | | 7:30PM | Cardinal Stritch | @ | Ashford University | 79-59 | |
| % | 18 | 1:00PM | Trinity International | @ | Chicago State University | 84-102 | |
| | Exhibition |
| | | 6:30PM | Purdue North Central | @ | Manchester College | 74-98 | |
| | | 7:00PM | University of Michigan-Dearborn | @ | Calumet St. Joseph | 79-84 | |
| | 20 | 4:00PM | Judson | vs. | Bethel College | 73-89 | |
| | Trinity International Classic - Bethel is #3 in NAIA National Poll |
| | | 5:00PM | Cardinal Stritch | vs. | Palm Beach Atlantic | 75-46 | |
| | Winona State Tournament |
| | | 6:00PM | Trinity Christian | @ | Marian College | 63-92 | |
| | Marian Tournament |
| | | 8:00PM | Missouri Valley College | vs. | Trinity International | 89-47 | |
| | LaQuinta Classic / Listen Live |
| | | 8:30PM | Calumet St. Joseph | @ | Fort Lewis College | 56-87 | |
| | Fort Lewis College Classic |
| | 21 | 1:00PM | Trinity Christian | vs. | Indiana - South Bend | 77-72 | |
| | Marian Tournament |
| | | 2:00PM | Holy Cross | @ | Purdue North Central | 77-87 | |
| | | 2:00PM | Judson | vs. | Missouri Valley College | 72-84 | |
| | Trinity International Classic |
| | | 4:00PM | Calumet St. Joseph | @ | New Mexico Highlands University | 71-94 | |
| | Fort Lewis College Classic |
| | | 6:00PM | Bethel College | vs. | Trinity International | 85-59 | |
| | LaQuinta Classic / Listen Live |
| | | 7:00PM | Cardinal Stritch | @ | Winona State University | 68-84 | |
| | Winona State Tournament |
| | 24 | 7:00PM | Purdue North Central | @ | Moody Bible Institute | 51-52 | |
| | | 7:00PM | Clarke College | @ | Judson | 98-93 | (OT) |
| | | 7:00PM | Trinity International | @ | Rockford College | 108-115 | |
| | Live Stats |
| | | 7:00PM | Indiana - South Bend | @ | Purdue Calumet | 69-68 | |
| | | 7:00PM | Cardinal Stritch | @ | Northland Baptist Bible College | 90-78 | |
| | | 7:30PM | Olivet Nazarene | @ | Trinity Christian | 78-69 | |
| | 25 | 6:00PM | Holy Cross | @ | Calumet St. Joseph | 81-100 | |
| | 27 | 5:00PM | Purdue North Central | vs. | Bemidji State University | 60-88 | |
| | UW-Parkside Tournament- Kenosha, WI |
| | | 7:00PM | Calumet St. Joseph | @ | Ohio Dominican College | 52-74 | |
| | 28 | 1:00PM | Purdue North Central | vs. | Grace Bible College | 82-97 | |
| | UW-Parkside Tournament- Kenosha, WI |
| | | 1:00PM | Calumet St. Joseph | @ | Shawnee State University | 78-76 | (OT) |
| | | 2:00PM | Purdue Calumet | @ | Taylor University | 75-84 | (OT) |
| December |
| | 1 | 7:00PM | Cornerstone University | @ | Judson | 88-82 | |
| | Cornerstone is #14 in the NAIA National Poll |
| | | 7:00PM | Cardinal Stritch | @ | Silver Lake College | 100-60 | |
| | | 7:30PM | Hope | @ | Trinity Christian | 97-80 | |
| | | 7:30PM | Trinity International | @ | St. Francis | 65-76 | |
| | 2 | 7:00PM | Trine University | @ | Purdue North Central | 69-62 | |
| | 3 | 7:00PM | Cardinal Stritch | @ | Wisconsin Lutheran College | 90-77 | |
| | | 7:30PM | Trinity International | @ | North Park University | 82-85 | |
| | Listen Live / Live Stats |
| | 4 | | Waldorf College | @ | Calumet St. Joseph | 65-72 | |
| | Crimson Wave Tournament |
| | | 6:00PM | Trinity Christian | vs. | East-West University | 83-93 | |
| | Saint Xavier Classic |
| | | 7:00PM | College of the Ozarks | @ | Judson | 87-81 | |
| | | 7:30PM | Purdue Calumet | @ | St. Francis | 83-77 | (OT) |
| | 5 | | Purdue North Central | @ | Silver Lake College | 61-57 | |
| | | | Bellevue University | @ | Calumet St. Joseph | 78-68 | |
| | Crimson Wave Tournament |
| | | 1:00PM | Trinity Christian | vs. | Indiana Wesleyan University | 64-88 | |
| | Saint Xavier Classic |
| | | 3:00PM | College of the Ozarks | @ | Trinity International | 70-60 | |
| | | 3:00PM | Tri-State University | @ | Purdue Calumet | 60-78 | |
| | | 7:30PM | Judson | @ | St. Francis | 102-92 | (2OT) |
| % | 8 | | Purdue North Central | @ | DePauw University | 70-92 | |
| | | 7:00PM | Saint Xavier | @ | Trinity International | 104-73 | |
| | | 7:00PM | Calumet St. Joseph | @ | Robert Morris | 92-101 | |
| | Listen Live on RSN |
| | 10 | 7:00PM | Purdue Calumet | @ | Indiana University Northwest | 81-73 | |
| | | 7:30PM | Moody Bible Institute | @ | Trinity Christian | 61-81 | |
| | 11 | | Purdue North Central | @ | Hope | 73-96 | |
| | Hope College Tournament - Holland, MI |
| | | 7:00PM | Calumet St. Joseph | @ | Concordia University | 77-83 | |
| | Bethal College Tourney Listen Live on RSN |
| | | 8:00PM | Cardinal Stritch | vs. | Indiana Institute of Technology | 78-70 | |
| | Taylor University Tournament |
| | 12 | | Purdue North Central | vs. | Marygrove College | 63-77 | |
| | Hope College Tournament - Holland, MI |
| | | | Calumet St. Joseph | @ | Kuyper College | 90-68 | |
| | Bethal College Tourney Listen Live on RSN |
| | | 2:00PM | Trinity International | @ | Indiana Wesleyan University | 72-88 | |
| | Live / Live Stats |
| | | 2:00PM | Cardinal Stritch | @ | Taylor University | 65-58 | |
| | Taylor University Tournament |
| | | 3:00PM | Indiana University East | @ | Purdue Calumet | 85-81 | |
| | | 3:00PM | Saint Xavier | @ | Trinity Christian | 92-84 | |
| | 15 | 6:00PM | Purdue North Central | @ | Concordia Theological Seminary | 94-22 | |
| % | | 7:00PM | Judson | @ | University of Wisconsin--Parkside | 74-98 | |
| | Exhibition Game |
| % | 16 | 7:00PM | Judson | @ | St. Cloud State | 68-102 | |
| | Exhibition Game |
| | 17 | 7:30PM | Cardinal Stritch | @ | St. Cloud State | 73-99 | |
| | 18 | 7:00PM | Cardinal Stritch | @ | Minnesota State-Mankato | 81-86 | |
| | | 7:30PM | Trinity Christian | @ | Calvin College | 59-86 | |
| % | | 8:00PM | Judson | @ | Concordia Minnesota | 78-110 | |
| | Exhibition Game |
| | 19 | 3:00PM | Purdue Calumet | @ | Saint Ambrose University | 52-83 | |
| | | 3:00PM | Judson | @ | Silver Lake College | 88-71 | |
| | | 7:00PM | Saint Xavier | @ | Purdue North Central | 74-63 | |
| | | 7:00PM | Carthage College | @ | Calumet St. Joseph | 90-88 | |
| | 22 | 2:00PM | Purdue North Central | @ | Marygrove College | 73-75 | |
| | | 6:00PM | Viterbo University | @ | Cardinal Stritch | 64-83 | |
| | | 7:00PM | Calumet St. Joseph | @ | Indiana University Northwest | 78-77 | |
| % | | 7:30PM | Purdue Calumet | @ | Lewis University | 71-90 | |
| % | 28 | 6:00PM | Purdue North Central | @ | Indiana-Purdue University-Fort Wayne | 55-101 | |
| | 29 | 7:00PM | Cardinal Stritch | @ | Dakota Wesleyan University | 70-62 | |
| | Dakota Wesleyan Classic |
| | | 7:30PM | Trinity Christian | @ | Lewis University | 73-95 | |
| | 30 | 4:00PM | Brescia University | @ | Purdue Calumet | 75-66 | |
| | | 5:00PM | Cardinal Stritch | vs. | Dana College | 92-74 | |
| | Dakota Wesleyan Classic |
| % | | 10:00PM | Trinity International | @ | Alaska-Anchorage | 57-87 | |
| | Watch Live / Live Stats |
| % | 31 | 8:00PM | Trinity International | @ | Alaska-Anchorage | 71-89 | |
| | Watch Live / Live Stats |
| January |
| % | 2 | 6:00PM | Judson | @ | Palm Beach Atlantic | 74-89 | |
| | Exhibition Game |
| | | 7:30PM | Trinity Christian | @ | St. Francis | 53-77 | |
| * | 6 | 7:00PM | Judson | @ | Purdue North Central | 83-73 | |
| * | | 7:00PM | Trinity International | @ | Purdue Calumet | 72-92 | |
| | Listen Live / Live Stats |
| * | | 7:30PM | Trinity Christian | @ | Cardinal Stritch | 78-91 | |
| * | 9 | 3:00PM | Purdue Calumet | @ | Trinity Christian | 85-96 | |
| * | | 5:00PM | Cardinal Stritch | @ | Judson | 78-62 | |
| | Cardinal Stritch is #23 in NAIA National Poll. |
| * | | 7:30PM | Calumet St. Joseph | @ | Trinity International | 76-99 | |
| | Listen Live |
| * | 13 | 4:00PM | Trinity International | @ | Purdue North Central | 101-92 | |
| * | | 7:30PM | Purdue Calumet | @ | Judson | 74-83 | |
| * | | 7:30PM | Calumet St. Joseph | @ | Trinity Christian | 73-69 | |
| | Webcast on Trinity LIVE! |
| * | 16 | 2:00PM | Trinity Christian | @ | Purdue North Central | 72-71 | |
| * | | 3:00PM | Judson | @ | Calumet St. Joseph | 98-82 | |
| | | 3:00PM | Holy Cross | @ | Purdue Calumet | 80-73 | |
| * | | 4:00PM | Trinity International | @ | Cardinal Stritch | 56-73 | |
| * | 20 | 7:00PM | Purdue North Central | @ | Purdue Calumet | 78-86 | |
| * | | 7:30PM | Trinity Christian | @ | Judson | 66-81 | |
| * | | 7:30PM | Cardinal Stritch | @ | Calumet St. Joseph | 89-57 | |
| | 21 | 7:30PM | Trinity International | @ | Olivet Nazarene | 58-86 | |
| * | 23 | 3:00PM | Purdue North Central | @ | Calumet St. Joseph | 79-76 | |
| * | | 3:00PM | Trinity International | @ | Trinity Christian | 85-98 | |
| | Live Webcast |
| * | | 4:00PM | Purdue Calumet | @ | Cardinal Stritch | 62-76 | |
| | | 7:00PM | Silver Lake College | @ | Judson | 61-108 | |
| | 25 | 7:00PM | Silver Lake College | @ | Cardinal Stritch | 68-95 | |
| | 27 | 6:00PM | Trinity Christian | @ | Holy Cross | 76-69 | |
| * | | 7:00PM | Cardinal Stritch | @ | Purdue North Central | 91-85 | |
| * | | 7:00PM | Calumet St. Joseph | @ | Purdue Calumet | 78-75 | |
| | Listen Live Crimson Wave Radio Network |
| * | | 7:30PM | Judson | @ | Trinity International | 89-72 | |
| | Listen Live |
| * | 30 | 3:00PM | Cardinal Stritch | @ | Trinity Christian | 79-76 | |
| | Webcast on Trinity LIVE! |
| * | | 5:00PM | Purdue North Central | @ | Judson | 71-98 | |
| * | | 7:30PM | Purdue Calumet | @ | Trinity International | 62-84 | |
| February |
| * | 3 | 7:00PM | Trinity Christian | @ | Purdue Calumet | 68-72 | |
| * | | 7:30PM | Trinity International | @ | Calumet St. Joseph | 70-88 | |
| * | | 7:30PM | Judson | @ | Cardinal Stritch | 67-90 | |
| | Cardinal Stritch is #10 in the NAIA Division II Poll. |
| | 5 | 5:00PM | Northland Baptist Bible College | @ | Cardinal Stritch | 53-69 | |
| | 6 | 2:00PM | Cardinal Stritch | @ | Holy Cross | 72-55 | |
| * | | 3:00PM | Judson | @ | Purdue Calumet | 85-71 | |
| * | | 3:00PM | Trinity Christian | @ | Calumet St. Joseph | 67-66 | |
| | WBCA Pink Zone |
| * | | 7:30PM | Purdue North Central | @ | Trinity International | 50-75 | |
| | 10 | 6:00PM | Purdue Calumet | @ | Holy Cross | 94-82 | |
| * | | 7:30PM | Purdue North Central | @ | Trinity Christian | PPD | |
| | Postponed to Feb. 11 |
| * | | 7:30PM | Cardinal Stritch | @ | Trinity International | 72-53 | |
| * | | 7:30PM | Calumet St. Joseph | @ | Judson | 62-83 | |
| | Listen Live Crimson Wave Radio Network |
| * | 11 | 7:30PM | Purdue North Central | @ | Trinity Christian | 70-84 | |
| * | 13 | 2:00PM | Purdue Calumet | @ | Purdue North Central | 113-116 | (OT) |
| * | | 3:00PM | Judson | @ | Trinity Christian | 78-73 | |
| | Webcast on Trinity LIVE! |
| * | | 4:00PM | Calumet St. Joseph | @ | Cardinal Stritch | 66-79 | |
| * | 17 | 7:00PM | Calumet St. Joseph | @ | Purdue North Central | 85-64 | |
| * | | 7:00PM | Cardinal Stritch | @ | Purdue Calumet | 80-68 | |
| * | | 7:30PM | Trinity Christian | @ | Trinity International | 86-81 | |
| | Listen Live |
| * | 20 | 3:00PM | Purdue Calumet | @ | Calumet St. Joseph | 78-74 | |
| * | | 5:00PM | Trinity International | @ | Judson | 100-107 | |
| | Live Stats |
| * | | 7:00PM | Purdue North Central | @ | Cardinal Stritch | 69-80 | |
| | 23 | 7:00PM | Purdue Calumet | @ | Calumet St. Joseph | 64-85 | |
| | CCAC Tournament - Quarterfinal Round |
| | | 7:00PM | Purdue North Central | @ | Judson | 78-86 | |
| | CCAC Tournament - Quarterfinal Round |
| | | 7:30PM | Trinity International | @ | Trinity Christian | 72-77 | |
| | CCAC Tournament - Quarterfinal Round |
| | 25 | 7:00PM | Calumet St. Joseph | @ | Cardinal Stritch | 59-91 | |
| | CCAC Tournament - Semifinal Round |
| | | 7:00PM | Trinity Christian | @ | Judson | 73-88 | |
| | CCAC Tournament - Semirfinal game |
| | 27 | 4:00PM | Judson | @ | Cardinal Stritch | 70-65 | |
| | CCAC Tournament - Championship |
| March |
| | 10 | 5:45PM | Judson | vs. | Oregon Institute of Technology | 57-63 | |
| | NAIA Division II National Tournament - Point Lookout, Missouri l Oregon Tech is #2 in NAIA |