| Year |
Runner, School, Time (distance) |
| 1954 |
Jim Schlaeppi, Central, 9:24.3 (1.8 miles) |
| 1965 |
Pat Kelly, Monroe, 9:39.1 (2 miles) |
| 1977 |
Don Hurley, Cretin, 15:00.8 (3 miles) |
| 2019 |
Oliver Paleen, Highland Park, 15:25.16 (5000 meters) |
| 2025 |
Charlie Loth, Como Park, 15:31.1 (5000 meters) |
|