Past Craftsman Truck Series winners at the Milwaukee Mile
| Date | Winner | Start | Make | Pole | Cautions | Laps | Avg. Speed | LC |
|---|
| 07-01-1995 | Mike Skinner | 1 | Chevrolet | 112.535 | 6 | 17 | 87.413 | 12 |
| 07-06-1996 | Jack Sprague | 8 | Chevrolet | 118.265 | 13 | 47 | 87.816 | 17 |
| 07-05-1997 | Ron Hornaday, Jr. | 5 | Chevrolet | 119.178 | 5 | 18 | 105.665 | 10 |
| 07-04-1998 | Mike Bliss | 2 | Ford | 120.53 | 4 | 16 | 104.347 | 8 |
| 07-03-1999 | Greg Biffle | 1 | Ford | 121.102 | 2 | 10 | 106.714 | 10 |
| 07-01-2000 | Kurt Busch | 1 | Ford | 120.518 | 7 | 32 | 89.264 | 10 |
| 06-30-2001 | Ted Musgrave | 3 | Dodge | 120.692 | 7 | 28 | 92.929 | 3 |
| 06-29-2002 | Terry Cook | 1 | Ford | 119.784 | 3 | 10 | 104.49 | 6 |
| 06-28-2003 | Brendan Gaughan | 2 | Dodge | 119.996 | 1 | 5 | 109.689 | 8 |
| 06-25-2004 | Ted Musgrave | 1 | Dodge | 121.98 | 8 | 45 | 83.23 | 9 |
| 06-24-2005 | Dennis Setzer | 3 | Chevrolet | 121.98 | 1 | 4 | 109.907 | 5 |
| 06-23-2006 | Johnny Benson, Jr. | 4 | Toyota | 122.021 | 9 | 37 | 85.673 | 12 |
| 06-22-2007 | Johnny Benson, Jr. | 4 | Toyota | 122.187 | 6 | 25 | 95.503 | 3 |
| 06-20-2008 | Johnny Benson, Jr. | 1 | Toyota | 121.082 | 6 | 27 | 89.686 | 10 |
| 06-20-2009 | Ron Hornaday, Jr. | 3 | Chevrolet | – | 5 | 23 | 95.012 | 8 |
| 08-27-2023 | Grant Enfinger | 1 | Chevrolet | 122.848 | 7 | 44 | 85.683 | 5 |
