The Dundee Invitational of 1999 was a cold, blistery day. As the boys varsity race was about to start, it began to sleet. Many runners were wearing gloves to keep their hands warm but kept the short shorts on. Brian Krohmer was once again able to go sub-18:00 and finished 16th.
Freshman Jake Heidkamp, who missed the bus ride to the meet, was forced to run in the junior high race because he missed the varsity start and nearly won it. In fact, he should've. He finished 3rd, but two kids from Hill-Murray cut the course short and got ahead of Jake and he never caught up.
AWARDS
Jake Heidkamp-3rd Place (Junior High)
Drew Ditlefsen-5th Place (Junior High)
Jim Meyer-7th Place (Junior High)
| Runner | Place | Time |
| 1. Brian Krohmer | 16th | 17:56 |
| 2. Matt Tucker | 21st | 18:17 |
| 3. Ben Dubay | 35th | 18:35 |
| 4. Drew Reiter | 49th | 18:57 |
| 5. Brandon Heebink | 50th | 18:58 |
| 6. Jeff Erickson | 57th | 19:30 |
| 7. Nic Sabatke | 65th | 20:17 |
| Runner | Place | Time |
| 1. David Johnson | 50th | 22:17 |
| 2. Matt Holland | 68th | 24:19 |
| 3. Greg Elsner | 69th | 25:30 |
| Runner | Place | Time |
| 1. Jake Heidkamp | 3rd | 12:29 |
| 2. Drew Ditlefsen | 5th | 13:19 |
| 3. Jim Meyer | 7th | 13:38 |
| 4. Brandon VanHee | 11th | 14:45 |
| 5. Matt Mullerleile | 17th | 15:07 |