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| 4/20/2019 | US 24 Speedway - Logansport, IN 1st race of the season Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 12th (DNF) |
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| 5/18/2019 | US 24 Speedway - Logansport, IN 2nd Annual Backing the Blue 1st pt night DOUBLE POINTS Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 8th | - | - | 17th |
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| 6/8/2019 | US 24 Speedway - Logansport, IN 2nd Point night A-Wing $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 9th | - | - | 15th (DNF) |
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| 7/5/2019 | US 24 Speedway - Logansport, IN rain out make up Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 9th |
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| 7/6/2019 | US 24 Speedway - Logansport, IN JR SPRINT $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Rain Out |
| 7/13/2019 | US 24 Speedway - Logansport, IN 4th pt night A Wing $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 9th | - | - | 15th (DNF) |
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| 7/20/2019 | US 24 Speedway - Logansport, IN 5th pt night Rest. Wing $300 to win Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 8th | - | - | 16th (DNF) |
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| 7/27/2019 | US 24 Speedway - Logansport, IN Outlaw Wing $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 5th | - | - | 11th (DNF) |
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| 8/3/2019 | US 24 Speedway - Logansport, IN 6th point race 2nd Annual Honoring Our Hero's Senior Class $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 14th |
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| 8/9/2019 | US 24 Speedway - Logansport, IN Triple XXX Root Beer Outlaw Wing #KINGOFTHEWING Preliminary night $1000 to win Winged Outlaw, Winged A-Class | Results | | Bob Dillon (Winged A-Class) | 5th | - | - | 7th |
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| 8/10/2019 | US 24 Speedway - Logansport, IN Triple XXX Root Beer Outlaw Wing #KINGOFTHEWING $8000 to win Winged Outlaw, Winged A-Class | Results | | Bob Dillon (Winged A-Class) | - | - | - | 8th |
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| 8/17/2019 | US 24 Speedway - Logansport, IN 7th pt night CAROL SMITH MEM. NW $1000 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 5th | - | - | 9th |
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| 8/31/2019 | US 24 Speedway - Logansport, IN 9th pt race Paul Moyer Memorial Jr Sprint class $300 to win, NW $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 7th | - | - | 11th |
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| 9/1/2019 | US 24 Speedway - Logansport, IN Senior Class $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 6th |
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| 9/14/2019 | US 24 Speedway - Logansport, IN 10th pt night Rest $300 to win Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 5th | - | - | 8th (DNF) |
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| 9/21/2019 | US 24 Speedway - Logansport, IN 11th pt night Non Wing $1000 to win Rest NW Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 7th |
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| 10/5/2019 | US 24 Speedway - Logansport, IN TBA Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 6th | - | - | 9th |
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| 10/12/2019 | US 24 Speedway - Logansport, IN T.B.A. Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Bob Dillon (Winged A-Class) | 7th (DNF) | - | - | 9th |
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