| Date | Location | Result | |
| Nov 13, 1999 | Danville, Ky. | Centre College 36, Rose-Hulman 14 | Box score |
| Nov 06, 1999 | Terre Haute, Ind. | DePauw University 33, Rose-Hulman 0 | Box score |
| Oct 30, 1999 | Phil Brown Field | Rose-Hulman 26, Earlham College 12 | Box score |
| Oct 16, 1999 | Jackson, Miss. | Millsaps College 35, Rose-Hulman 28 | Box score |
| Oct 09, 1999 | Memphis, Tenn. | Rhodes College 51, Rose-Hulman 14 | Box score |
| Oct 02, 1999 | Terre Haute, Ind. | Trinity University 51, Rose-Hulman 0 | Box score |
| Sep 25, 1999 | Kalamazoo, Mich. | Rose-Hulman 20, Kalamazoo College 15 | Box score |
| Sep 18, 1999 | Terre Haute, Ind. | Univ. of Chicago 22, Rose-Hulman 20 | Box score |
| Sep 11, 1999 | Terre Haute, Ind. | Univ. of the South 44, Rose-Hulman 15 | Box score |
| Sep 04, 1999 | St. Louis, Mo. | Washington Univ. 25, Rose-Hulman 13 | Box score |