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| 5/11/2019 | Rice Lake Speedway - Rice Lake, WI Trackside Collectibles 40, WISSOTA Late Models $2,000-To-Win DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 7th | - | - | 20th (DNF) |
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| 5/25/2019 | Hibbing Raceway - Hibbing, MN Hibbing City Merchants Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 4th | - | - | 3rd |
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| 5/31/2019 | Gondik Law Speedway - Superior, WI Rescheduled Season Opener WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 1st |
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| 6/1/2019 | Hibbing Raceway - Hibbing, MN Quad Cities Merchants Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 7th | - | - | 5th |
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| 6/2/2019 | Proctor Speedway - Proctor, MN Meet the Drivers Night - Points Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 2nd |
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| 6/7/2019 | Red Cedar Speedway - Menomonie, WI Street Stock Bonus Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 4th | - | - | 9th |
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| 6/8/2019 | Hibbing Raceway - Hibbing, MN Iron Mining Association Night plus Kids Bicycle Races Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 1st | - | - | 8th |
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| 6/13/2019 | Grand Rapids Speedway - Grand Rapids, MN Grand Rapids Merchants (Kid Bus Rides) WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 4th |
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| 6/14/2019 | Gondik Law Speedway - Superior, WI Meet The Drivers Night/SHS Dance Team Face Painting Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 4th |
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| 6/15/2019 | Hibbing Raceway - Hibbing, MN Fortune Bay Resort Casino Night plus Kids Box Car Races Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 4th | - | - | 6th |
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| 6/16/2019 | Proctor Speedway - Proctor, MN Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 6th | - | - | 5th |
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| 6/22/2019 | Hibbing Raceway - Hibbing, MN Rene Hughes Memorial Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Winged Sprints, Non-Winged Sprints, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 1st | - | - | 1st |
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| 6/29/2019 | Gondik Law Speedway - Superior, WI 3rd Annual Great Lakes Border Battle-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 6th | - | - | 16th |
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| 6/30/2019 | Gondik Law Speedway - Superior, WI 3rd Annual Great Lakes Border Battle-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 8th |
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| 7/5/2019 | Hibbing Raceway - Hibbing, MN 3rd Annual Firecracker Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 1st | - | - | 4th |
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| 7/7/2019 | Proctor Speedway - Proctor, MN Halvor Lines Trucking Military Night - Points Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 2nd |
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| 7/11/2019 | Grand Rapids Speedway - Grand Rapids, MN 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 6th |
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| 7/12/2019 | Gondik Law Speedway - Superior, WI Regular Race Night Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 7th | - | - | 15th (DNF) |
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| 7/14/2019 | Proctor Speedway - Proctor, MN Hornet Nationals - Fair Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 5th |
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| 7/16/2019 | Gondik Law Speedway - Superior, WI Fair Week-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 5th | - | - | 10th |
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| 7/20/2019 | Hibbing Raceway - Hibbing, MN Chisholm City Merchants Night plus Power Wheels Races Vintage Modifieds, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 1st | - | - | 8th |
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| 7/26/2019 | Gondik Law Speedway - Superior, WI AMSOIL Twin Ports Twin 25s/WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 13th |
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| 7/27/2019 | Hibbing Raceway - Hibbing, MN Radko Iron and Supply Night plus Meet the Drivers!!!!! Vintage Modifieds, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 7th (DNF) | - | - | 7th |
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| 8/1/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 1st | - | - | 12th (DNF) |
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| 8/2/2019 | Proctor Speedway - Proctor, MN Monohan Pure Stock Special - Points Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 4th | - | - | 2nd |
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| 8/9/2019 | Gondik Law Speedway - Superior, WI Hall of Fame Night/AFCO Race of Champions Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 4th | - | - | 12th (DNF) |
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| 8/10/2019 | Hibbing Raceway - Hibbing, MN Weekly Racing plus Hall of Fame Induction Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 10th |
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| 8/11/2019 | Proctor Speedway - Proctor, MN Northern Renegades Sprint Cars - Points Race Non-Winged Sprints, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 5th | - | - | 9th |
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| 8/15/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 2nd |
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| 8/17/2019 | Hibbing Raceway - Hibbing, MN Bud Light Season Championship Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 5th |
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| 8/18/2019 | Proctor Speedway - Proctor, MN Championship Night - Points Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 6th | - | - | 11th |
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| 8/22/2019 | Grand Rapids Speedway - Grand Rapids, MN 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 3rd | - | - | 7th |
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| 8/23/2019 | Gondik Law Speedway - Superior, WI Season Championship/Adult Trike Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 10th |
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| 8/29/2019 | Proctor Speedway - Proctor, MN 47th Annual Silver 1000 WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Modifieds | Results | | Terry Lillo (WISSOTA Late Model) | 5th | - | - | 23rd (DNF) |
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| 8/30/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA CLASSIC - WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 7th (DNF) | - | - | 24th |
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| 8/31/2019 | Hibbing Raceway - Hibbing, MN Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 8th (DNF) | - | 6th | 12th |
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| 9/1/2019 | Hibbing Raceway - Hibbing, MN Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Terry Lillo (WISSOTA Late Model) | 7th | - | - | 13th |
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| 9/7/2019 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #3 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Terry Lillo (WISSOTA Late Model) | 2nd | - | - | 4th |
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