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| 5/22/2020 | Mississippi Thunder Speedway - Fountain City, WI USMTS Spring Shootout and Rumble by the River 40 Presented by Coca-Cola A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Jeff Massingill (Dirt Late Models) | 4th | - | 1st | 26th (DNF) |
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| 5/29/2020 | Gondik Law Speedway - Superior, WI Rescheduled 59th Season Opener USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 6th | - | - | 5th |
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| 5/30/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds | Results | | Jeff Massingill (Dirt Late Models) | 3rd | - | - | 3rd |
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| 6/5/2020 | Gondik Law Speedway - Superior, WI Gondik Law Speedway Doubleheader Shootout presented by Broking Transport-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 1st | - | - | 8th |
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| 6/6/2020 | Rice Lake Speedway - Rice Lake, WI WISSOTA Late Models plus Supers, Streets, MWM, and Pures no Mods DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 2nd | - | - | 13th (DNF) |
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| 6/11/2020 | Cedar Lake Speedway - New Richmond, WI MASTERS Day 1 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Jeff Massingill (Dirt Late Models) | 3rd | - | - | 4th |
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| 6/12/2020 | Cedar Lake Speedway - New Richmond, WI MASTERS Day 2 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Jeff Massingill (Dirt Late Models) | 4th | - | 2nd | 21st |
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| 6/13/2020 | Cedar Lake Speedway - New Richmond, WI Masters Day 3 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Jeff Massingill (Dirt Late Models) | 1st | - | - | 6th |
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| 6/19/2020 | Gondik Law Speedway - Superior, WI Rivord Auto & Transmission Repair Night DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 2nd | - | - | 4th |
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| 6/26/2020 | River Cities Speedway - Grand Forks, ND Premier Racing Series 410 Sprints - Winged, B Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 3rd |
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| 6/27/2020 | Hibbing Raceway - Hibbing, MN Season Opener! Limited Sprints - Winged: Upper Midwest Sprint Car Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 1st | - | - | 13th |
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| 6/28/2020 | Gondik Law Speedway - Superior, WI Sunday Night at the Speedway 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 5th | - | - | 5th |
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| 7/2/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Dirt Super Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | - | - | 4th | 20th |
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| 7/3/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | 6th | - | - | 20th (DNF) |
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| 7/4/2020 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | 7th | - | - | 20th (DNF) |
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| 7/10/2020 | Outagamie Speedway - Seymour, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models IMCA Modified, IMCA Stock Car | Results | | Jeff Massingill (Dirt Super Late Models) | 7th | - | 5th | - |
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| 7/11/2020 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | 6th | - | 5th | - |
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| 7/14/2020 | Gondik Law Speedway - Superior, WI World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods, WISSOTA Hornet | Results | | Jeff Massingill (Dirt Super Late Models) | 6th | - | 3rd | 18th |
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| 7/18/2020 | Red River Valley Speedway - West Fargo, ND World of Outlaw Late Models Dirt Super Late Models: World of Outlaws - Late Models Sprint Cars, Stock Cars, B Modifieds, Dirt Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | 8th (DNF) | - | 3rd | 16th |
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| 7/19/2020 | River Cities Speedway - Grand Forks, ND Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Jeff Massingill (Dirt Super Late Models) | 5th | - | - | 14th |
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| 7/25/2020 | Hibbing Raceway - Hibbing, MN Hornet Swarm Vintage Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 7th (DNF) | - | - | 2nd |
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| 7/30/2020 | Grand Rapids Speedway - Grand Rapids, MN Thursday Night Thunder Racing Action WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 2nd |
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| 7/31/2020 | Gondik Law Speedway - Superior, WI Structural Buildings WISSOTA Late Model Challenge Series USRA Late Models, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 2nd | - | - | 4th |
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| 8/1/2020 | Rice Lake Speedway - Rice Lake, WI Structural Buildings WISSOTA Late Model Challenge Series DIRTcar UMP Modifieds, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 11th |
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| 8/6/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Jeff Massingill (Dirt Super Late Models) | 12th (DNF) | - | 14th (DNF) | - |
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| 8/7/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Dirt Late Models, USRA Modifieds | Results | | Jeff Massingill (Dirt Super Late Models) | DNS | - | - | - | | Jeff Massingill (Dirt Late Models) | 3rd | - | - | 10th |
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| 8/8/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, USRA Modifieds | Results | | Jeff Massingill (Dirt Super Late Models) | - | - | DNS | - | | Jeff Massingill (Dirt Late Models) | 5th | - | - | 10th |
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| 8/15/2020 | Hibbing Raceway - Hibbing, MN Weekly Racing Vintage Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 6th | - | - | 10th |
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| 8/20/2020 | Grand Rapids Speedway - Grand Rapids, MN Thursday Night Thunder Racing Action WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 1st | - | - | 3rd |
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| 8/21/2020 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown Presented by Hurco/Stone Machinery Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Jeff Massingill (Dirt Late Models) | 4th | - | - | - |
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| 8/22/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #14 & Season Championship 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series DIRTcar UMP Modifieds, A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Jeff Massingill (Dirt Late Models) | 5th | - | 3rd | 7th |
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| 8/28/2020 | Mississippi Thunder Speedway - Fountain City, WI 12th Annual Season Championship Night Dirt Late Models, Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Jeff Massingill (Dirt Late Models) | 6th | - | - | 13th |
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| 8/29/2020 | Ogilvie Raceway - Ogilvie, MN Track Championship w/ Wissota Late Model USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 3rd |
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| 9/3/2020 | ABC Raceway - Ashland, WI Prelude to the Clay USRA Modifieds, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 1st |
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| 9/4/2020 | Grand Rapids Speedway - Grand Rapids, MN Structural Buildings WISSOTA Late Model Challenge Series USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 4th | - | - | 4th |
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| 9/5/2020 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 1st | - | - | 6th |
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| 9/6/2020 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 1st | - | - | 3rd |
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| 9/10/2020 | River Cities Speedway - Grand Forks, ND Prelude to the Johnny - NLRA Late Model Tour Championship B Modifieds, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | 4th |
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| 9/11/2020 | River Cities Speedway - Grand Forks, ND John Seitz Memorial Night 1 - Blazin' Challenge NOSA Sprints 410 Sprints - Winged, B Modifieds, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 7th | - | 4th | 5th |
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| 9/17/2020 | I-94 Speedway - Fergus Falls, MN The Dick Johanneck King of Dirt Special Hornets, Economy Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | - |
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| 9/18/2020 | I-94 Speedway - Fergus Falls, MN The Dick Johanneck King of Dirt Special Hornets, Economy Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | 7th | 2nd | - | - |
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| 9/19/2020 | I-94 Speedway - Fergus Falls, MN The Dick Johanneck King of Dirt Special Hornets, Economy Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jeff Massingill (WISSOTA Late Model) | - | - | - | 2nd |
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| 9/25/2020 | Jamestown Speedway - Jamestown, ND 49th Annual Jamestown Stock Car Stampede A Modifieds, Midwest Modifieds, B Modifieds, Street Stocks, Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock, Junior Slingshots | Results | | Jeff Massingill (WISSOTA Late Model) | 4th | - | - | 6th |
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| 9/26/2020 | Jamestown Speedway - Jamestown, ND 49th Annual Jamestown Stock Car Stampede A Modifieds, Midwest Modifieds, B Modifieds, Street Stocks, Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock, Junior Slingshots | Results | | Jeff Massingill (WISSOTA Late Model) | 4th | - | - | 20th (DNF) |
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| 10/2/2020 | ABC Raceway - Ashland, WI Red Clay Classic WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Canceled |
| 10/9/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | 3rd | - | - | - |
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| 10/10/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jeff Massingill (WISSOTA Late Model) | - | - | - | 7th |
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