12 Games
- Conference games only
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
|---|---|---|---|---|---|---|---|---|
| 1 | Oct 14, 1899 | Sat | Wisconsin | 38 | Northwestern | 0 | ||
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 2 | Oct 28, 1899 | Sat | Michigan | 5 | @ | Illinois | 0 | |
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 3 | Nov 4, 1899 | Sat | Chicago | 44 | Purdue | 0 | ||
| 4 | Nov 4, 1899 | Sat | Northwestern | 11 | @ | Minnesota | 5 | |
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 5 | Nov 11, 1899 | Sat | Chicago | 76 | Northwestern | 0 | ||
| 6 | Nov 11, 1899 | Sat | Wisconsin | 23 | Illinois | 0 | ||
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 7 | Nov 18, 1899 | Sat | Wisconsin | 19 | @ | Minnesota | 0 | |
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 8 | Nov 22, 1899 | Wed | Purdue | 5 | @ | Illinois | 0 | |
| 9 | Nov 25, 1899 | Sat | Chicago | 29 | Minnesota | 0 | ||
| 10 | Nov 25, 1899 | Sat | Northwestern | 29 | Purdue | 0 | ||
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 11 | Nov 30, 1899 | Thu | Wisconsin | 17 | N | Michigan | 5 | |
| Rk | Date | Day | Winner | Pts | Loser | Pts | Notes | |
| 12 | Dec 9, 1899 | Sat | Chicago | 17 | @ | Wisconsin | 0 |
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