1999 depauw football schedule/results (5-5, 3-3 scac)
| Sept. 4 | *RHODES (Community Day) | L, 14-33 |
| Sept. 11 | ILLINOIS WESLEYAN (Hall of Fame Day) | L, 20-28 |
| Sept. 18 | at Hope | W, 27-21 |
| Sept. 25 | *at Trinity | L, 0-44 |
| Oct. 2 | at Chicago | L, 6-9 (2OT) |
| Oct. 9 | *at Sewanee | L, 14-33 |
| Oct. 23 | *MILLSAPS | W, 41-10 |
| Oct. 30 | *CENTRE | W, 26-23 |
| Nov. 6 | *at Rose-Hulman | W, 33-0 |
| Nov. 13 | WABASH (Monon Bell) | W, 21-7 |
| *indicates Southern Collegiate Athletic Conference games | ||