| | Day | Time | | Opponent | Score | |
| October |
| | 29 | 7:00PM | @ | Trinity International University | W-99-79 | |
| November |
| | 1 | 4:00PM | @ | Mid-Continent College | W-80-72 | |
| | 5 | 7:00PM | @ | Lindenwood University | W-82-77 | |
| | 7 | 7:00PM | vs. | Ohio Dominican University | W-88-86 | |
| | 11 | 7:00PM | @ | Park | L-64-79 | |
| | 14 | 7:00PM | vs. | Indiana University-South Bend | W-75-61 | |
| | McKendree Classic |
| | 15 | 7:00PM | vs. | Union University | L-80-83 (OT) | |
| | McKendree Classic |
| | 19 | 7:00PM | vs. | Mid-Continent College | W-89-70 | |
| | 22 | 4:00PM | @ | Benedictine College | L-57-72 | |
| | 25 | 7:00PM | vs. | Brescia University | W-75-63 | |
| | 28 | 6:00PM | vs. | Freed-Hardeman University | L-79-80 | |
| | Union University Thanksgiving Classic |
| | 29 | 4:00PM | @ | Union University | W-67-66 | |
| | Union University Thanksgiving Classic |
| December |
| | 6 | 7:00PM | vs. | Park | W-78-76 | |
| | 9 | 7:00PM | @ | Olivet Nazarene University | W-78-75 (OT) | |
| | McKendree's Harry Statham wins game No. 975 and ties Jim Phelan as the all-time leader in games coached at the four-year level |
| | 16 | 7:00PM | @ | Concordia Seminary-St. Louis | W-70-48 | |
| | McKendree coach Harry Statham becomes the all-time leader for games coached at the four-year collegiate level, all divisions (1,355 games) |
| | 30 | 3:00PM | @ | Ohio Dominican University | W-63-59 | |
| January |
| * | 8 | 7:30PM | vs. | William Woods | W-74-69 | |
| * | 10 | 4:00PM | @ | Missouri Baptist | W-80-72 | |
| * | 15 | 7:30PM | @ | Harris-Stowe | W-76-62 | |
| * | 20 | 7:30PM | @ | Columbia | W-68-65 | |
| * | 22 | 7:30PM | vs. | Williams Baptist | W-84-68 | |
| * | 24 | 4:00PM | @ | Hannibal-LaGrange | W-68-65 | |
| * | 31 | 4:00PM | vs. | University of Illinois at Springfield | W-82-74 | |
| | McKendree's Eric Palm scores a season-high 36 points to lead the Bearcats to their 12th consecutive win |
| February |
| * | 5 | 7:30PM | @ | William Woods | W-66-46 | |
| * | 7 | 4:00PM | vs. | Missouri Baptist | W-76-56 | |
| * | 12 | 7:30PM | vs. | Harris-Stowe | W-86-61 | |
| | Bearcats collect their 15th consecutive win |
| * | 17 | 7:30PM | vs. | Columbia | W-55-53 | |
| * | 19 | 7:30PM | @ | Williams Baptist | W-71-52 | |
| | McKendree clinches AMC regular-season title for second consecutive year |
| * | 21 | 4:00PM | vs. | Hannibal-LaGrange | W-77-64 | |
| | Coach Harry Statham earns career win No. 990; Bearcats win 18th consecutive game |
| * | 28 | 4:00PM | @ | University of Illinois at Springfield | W-80-69 | |
| | McKendree wins its 19th consecutive game and finishes AMC play with a 14-0 record |
| March |
| | 5 | 7:00PM | vs. | Harris-Stowe | W-79-50 | |
| | AMC Men's Basketball Tournament -- Quarterfinal Round |
| | 7 | 4:00PM | vs. | Hannibal-LaGrange | W-79-63 | |
| | AMC Men's Basketball Tournament -- Semifinal Round |
| | 10 | 7:00PM | vs. | Columbia | L-54-65 | |
| | AMC Men's Basketball Tournament -- Championship |
| | 19 | 8:00PM | vs. | Northwestern Oklahoma State University | W-83-58 | |
| | 2009 Buffalo Funds-NAIA Division I Men's Basketball National Championship -- First Round |
| | 20 | 9:45PM | vs. | Texas Wesleyan University | W-87-75 | |
| | 2009 Buffalo Funds-NAIA Division I Men's Basketball National Championship -- Second Round |
| | 21 | 8:00PM | vs. | MidAmerica Nazarene University | L-55-59 | |
| | 2009 Buffalo Funds-NAIA Division I Men's Basketball National Championship -- Quarterfinals |
