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| 4/23/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #1 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 5th (DNF) | - | - | 6th (DNF) |
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| 4/24/2021 | Newton Kart Klub - Newton, IA NKK Points Night #1 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 4th (DNF) | - | - | DNS |
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| 4/30/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #2 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 4th | - | - | 8th |
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| 5/7/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #3 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 3rd | - | - | 3rd |
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| 5/14/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #4 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | DNS | - | - | 5th |
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| 6/4/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #5 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | DNS | - | - | 5th |
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| 6/5/2021 | Newton Kart Klub - Newton, IA NKK Points Night #4 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 4th | - | - | 4th |
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| 6/19/2021 | Newton Kart Klub - Newton, IA NKK Points Night #5 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Junior 2 Heavy Dirt Karts, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 3rd | - | - | 5th |
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| 7/2/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #8 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 5th | - | - | 6th |
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| 7/10/2021 | Golden Spike Speedway - Blue Earth, MN Points Race Junior 1 Lites Dirt Karts, Winged Outlaw, Adult Open, Adult Heavy, Adult Lites, Rookie Class, Junior 2 Super Stock, Flat Adult Clone Heavy, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, Kid Karts Dirt, 125 Winged Outlaw, Flat Jr. 1 Clone, Predator Maxxis | Results | | Anthony Guessford Jr (500 Winged Open Outlaw) | - | - | - | - |
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| 7/16/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #9 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 3rd | - | - | 6th |
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| 7/17/2021 | Newton Kart Klub - Newton, IA NKK Points Night #7 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Animal Lites, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 6th (DNF) | - | - | 5th |
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| 7/23/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #10 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 3rd | - | - | 5th |
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| 7/30/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #11 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Rain Out |
| 7/31/2021 | Newton Kart Klub - Newton, IA NKK Points Night #8 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Animal Lites, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 5th (DNF) | - | - | 5th |
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| 8/9/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 5th | - | - | - |
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| 8/10/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | - | - | - | 12th (DNF) |
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| 8/21/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #12 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Anthony Guessford Jr (Adult Medium) | 5th | - | - | 7th (DNF) |
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| 8/28/2021 | Newton Kart Klub - Newton, IA NKK Championship Night Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Junior 2 Heavy Dirt Karts, Animal Lites, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Anthony Guessford Jr (250 Winged Outlaw) | 3rd | - | - | DNS |
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| 9/25/2021 | Newton Kart Klub - Newton, IA NKK King of the Corn Rotax Micro Max, Mini 60, Tag Cadet, Junior 1 Heavy Dirt Karts, Animal Lites, Adult Open, Adult Medium, Yamaha Open, Junior Kohler Cage, Junior Midget, Sportsman Midget, Comer 50CC, Briggs 206, Kid Karts, 250 yamaha, Champ Kart, Junior 1 Lites Asphalt Karting, Junior 3 Lites Asphalt Karting, Junior Camp Asphalt Karting, Senior Camp Asphalt Karting, Open Asphalt Karting, Junior 1 Medium Asphalt Karting, Junior 1 Heavy Asphalt Karting, Junior 1 Animal Asphalt Karting, Junior 2 Medium Asphalt Karting, Junior 2 Heavy Asphalt Karting, Junior 2 Animal Asphalt Karting, Junior 2 Lites Asphalt Karting, Junior 3 Medium Asphalt Karting, Junior 3 Heavy Asphalt Karting, Junior 3 Animal Asphalt Karting, 125 Winged Outlaw | Results | | Anthony Guessford Jr (Yamaha Open) | DNS | - | - | 4th (DNF) | | Anthony Guessford Jr (Junior 3 Medium Asphalt Karting) | 4th | - | - | DNS |
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| 10/2/2021 | Cedar Lake Speedway Indoor Arena - New Richmond, WI Melvin Germain Memorial & Rumble at the Arena Series Final Night! Junior 2 Medium Dirt Karts, Junior 2 Heavy Dirt Karts, Animal Heavy, Rookie Class, Junior 1 Animal Dirt Karts, Junior Kohler Cage, Restricted Box Stock, Unrestricted Box Stock, 250 yamaha, Flat Jr. 3 Clone Heavy, Flat Adult Clone Heavy, 250 Winged Outlaw Heavy, Cage Jr. Sprints, LO 206 Dirt Karts, Junior 3 Medium Dirt Karts, Flat Jr. 1 Clone Heavy, Flat Jr. 1 Clone | Results | | Anthony Guessford Jr (250 Winged Outlaw Heavy) | - | - | - | 1st |
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