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| Past Champions | Track Records |
The Dairyland Classic traces its roots back to June 7, 1985, when motorcycle racing first visited the Sheboygan County Fairgrounds’ new 1/3-mile clay oval. The racing was sanctioned through the American Motorcyclist Association (AMA) as a Pro-Am event, featuring several amateur and professional racing classes combined in a single event. Similar racing formats were used in the annual June races through 1998 first as Pro-Am sanctions then as semi-pro sanctions.
On June 11, 1999, the first ever Dairyland Classic Short Track National was scheduled as a round of the AMA’s Grand National Championship series, which was the premier professional dirt track series at that time. The new name honored a group of Wisconsin Harley-Davidson dealer enthusiasts who agreed to finance the increased fees associated with a National Championship event. Unfortunately, inclement weather forced the cancellation of the event shortly after the completion of practice.
On June 22, 2000, the second annual Dairyland Classic hosted a round of the AMA’s Hot Shoe series, which is the professional series beneath the Grand National Championship series. The later-than-usual date was chosen to coincide with the National H.O.G. Rally taking place in Milwaukee.
On June 8, 2001, the third annual Dairyland Classic Short Track National hosted Round 2 of the Drag Specialties National Dirt Track Series, sanctioned by Formula USA. A near-capacity crowd cheered enthusiastically as decent weather allowed the completion of the first National Championship dirt track series event held in Wisconsin since 1966. Formula USA-sanctioned National events followed on June 8, 2002 and June 7, 2003, the latter event serving as the opening round of the Formula USA National series.
On June 4, 2004, the Dairyland Classic returned to its roots as a semi-pro event running on the Friday evening of Road America's AMA Superbike Weekend. In June 3, 2005, the event upgraded to a Pro-Am sanction, enabling it to draw seven of the top 10 professional racers in the country, plus 3,000 fans. The June 2, 2006 edition witnessed nine of the top 10 professional racers competing, including the defending National Champion Chris Carr. The June 1, 2007 event drew eleven of the top 50 competitors, many of whom competed in a National Championship event in Tennessee the following evening.
Efforts to run the June 6, 2008 event were submerged by the wettest month in Wisconsin history. However, the rescheduled event held on August 22 featured the driest weather in years. The June 5, 2009 event featured the best weather to date. The June 4, 2010 event ran without incident despite constant rain until noon on race day.
| YEAR | # | NAME | HOMETOWN | MOTORCYCLE | SANCTION |
| 2010 | 21 | Jared Mees | Clio, MI | Honda CRF450R | AMA Standard |
| 2009 | 21 | Jared Mees | Clio, MI | Honda CRF450R | AMA Pro-Am |
| 2008 | 1 | Kenny Coolbeth | Morris, CT | Honda CRF450R | AMA Pro-Am |
| 2007 | 11 | Bryan Bigelow | Au Gres, MI | Suzuki RM-Z450 | AMA Pro-Am |
| 2006 | 28 | Shaun Russell | San Jose, CA | Rotax 450cc | AMA Pro-Am |
| 2005 | 28 | Shaun Russell | San Jose, CA | Rotax 505cc | AMA Pro-Am |
| 2004 | 69W | Jethro Halbert | Graham, WA | Rotax 505cc | AMA Semi-Pro |
| 2003 | 31 | Kenny Coolbeth | Warren, CT | KTM 450cc | Formula USA National |
| 2002 | 3 | Joe Kopp | Mica, WA | KTM 450cc | Formula USA National |
| 2001 | 80 | Rich King | Dyasrt, IA | Buell Blast 500cc | Formula USA National |
| 2000 | 1 | Chris Carr | Fleetwood, PA | Rotax 600cc | AMA Hot Shoe |
| 1999 | - - - - Rained Out - - - - | AMA Grand National | |||
| YEAR | # | NAME | HOMETOWN | MOTORCYCLE | SANCTION |
| 1998 | 33 | JR Schnabel | West Bend, WI | Rotax 600cc | AMA Semi-Pro |
| 1997 | 33 | JR Schnabel | West Bend, WI | Rotax 600cc | AMA Semi-Pro |
| 1996 | 15K | JR Schnabel | West Bend, WI | Rotax 600cc | AMA Semi-Pro |
| 1995 | 16L | JR Schnabel | West Bend, WI | Rotax 600cc | AMA Semi-Pro |
| 1994 | 45 | Jim Sumner | Milwaukee, WI | Rotax 600cc | AMA Semi-Pro |
| 1993 | 50Z | Matt Wait | Lodi, CA | Rotax 600cc | AMA Semi-Pro |
| 1992 | 94K | Steve Champine | Green Bay, WI | Rotax 600cc | AMA Pro-Am |
| 1991 | 76 | Steve Kasten | Hatley, WI | Yamaha 600cc | AMA Pro-Am |
| 1990 | 76 | Steve Kasten | Hatley, WI | Yamaha 600cc | AMA Pro-Am |
| 1989 | 10Y | Andy Tresser | Redwood City, CA | Rotax 600cc | AMA Pro-Am |
| 1988 | 10Y | Andy Tresser | Redwood City, CA | Rotax 600cc | AMA Pro-Am |
| 1987 | 48P | Mark Gruber | Waukegan, IL | Rotax 600cc | AMA Pro-Am |
| 1986 | 48P | Mark Gruber | Waukegan, IL | Rotax 600cc | AMA Pro-Am |
| 1985 | 48P | Mark Gruber | Waukegan, IL | Rotax 500cc | AMA Pro-Am |
| Record | # | NAME | HOMETOWN | DATE | TIME | MOTORCYCLE |
| 1-lap track record | 22 | Nick Cummings | Mount Morris, MI | June 1, 2007 | 0:15.311 (78.375 mph) | Custom-framed Suzuki RM-Z450 |
| 6-lap track record | 14 | Jake Johnson | Franklinville, NJ | August 22, 2008 | 1:44.355 (68.995 mph) | Custom-framed Suzuki RM-Z450 |
| 8-lap track record | 69 | Jethro Halbert | San Jose, CA | August 22, 2008 | 2:15.772 (70.707 mph) | Custom-framed Honda CR450R |
| 20-lap track record | 1 | Kenny Coolbeth | Morris, CT | August 22, 2008 | 5:40.589 (70.466 mph) | Custom-framed Honda CR450R |
| DATE | # | NAME | HOMETOWN | MOTORCYCLE | TIME | SPEED |
| June 4, 2010 | 3 | Joe Kopp | Mica, WA | Production-framed Honda CRF450R | 17.252 seconds | 69.557 mph |
| June 5, 2009 | 21 | Jared Mees | Clio, MI | Production-framed Honda CRF450R | 16.655 seconds | 72.050 mph |
| August 22, 2008 | 21 | Jared Mees | Clio, MI | Custom-framed Honda CRF450R | 16.118 seconds | 74.451 mph |
| June 1, 2007 | 22 | Nick Cummings | Mount Morris, MI | Custom-framed Suzuki RM-Z450 | 15.311 seconds | 78.375 mph |
| June 2, 2006 | 31 | Kenny Coolbeth | Warren, CT | Custom-framed Honda CRF450R | 15.731 seconds | 76.282 mph |
| June 3, 2005 | 3 | Joe Kopp | Mica, WA | Custom-framed KTM 505cc | 17.038 seconds | 70.429 mph |
| June 4, 2004 | 3 | Joe Kopp | Mica, WA | Custom-framed KTM 505cc | 17.025 seconds | 70.484 mph |
| June 7, 2003 | 31 | Kenny Coolbeth | Warren, CT | Production-framed KTM 450cc | 16.249 seconds | 73.857 mph |
| June 8, 2002 | 3 | Joe Kopp | Mica, WA | Production-framed KTM 450cc | 17.465 seconds | 68.709 mph |
| June 8, 2001 | 80 | Rich King | Dysart, IA | Custom-framed Buell 500cc | 17.469 seconds | 68.693 mph |