| | Heat | Dash | B Feature | A Feature |
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| 2/13/2014 | Volusia Speedway Park - De Leon Springs, FL 410 Sprints - Winged: All Star Circuit of Champions | Results | | Jason Sides (410 Sprints - Winged) | 11th | - | 22nd | - |
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| 2/14/2014 | Volusia Speedway Park - De Leon Springs, FL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 9th |
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| 2/15/2014 | Volusia Speedway Park - De Leon Springs, FL 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 21st |
|
| 2/16/2014 | Volusia Speedway Park - De Leon Springs, FL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 16th |
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| 2/20/2014 | East Bay Raceway Park - Tampa, FL | Results | | Jason Sides (360 Sprints - Winged) | - | - | - | 5th |
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| 2/22/2014 | East Bay Raceway Park - Tampa, FL | Results | | Jason Sides (360 Sprints - Winged) | - | - | - | 4th |
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| 3/5/2014 | Las Vegas Motor Speedway - Las Vegas, NV 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: USAC 360 Sprint Series | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 9th | - | 18th |
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| 3/6/2014 | Las Vegas Motor Speedway - Las Vegas, NV 3rd Annual Sin City Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: USAC 360 Sprint Series with USAC Southwest | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 3rd | - | 4th |
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| 3/8/2014 | CS Raceway - Tucson, AZ 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 19th |
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| 3/14/2014 | Thunderbowl Raceway - Tulare, CA 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: USAC 360 Sprint Series | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 4th | 18th |
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| 3/15/2014 | Thunderbowl Raceway - Tulare, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 7th | - |
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| 3/22/2014 | Stockton Dirt Track - Stockton, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 6th | - | 13th |
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| 3/28/2014 | Merced Speedway - Merced, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 15th |
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| 4/5/2014 | Calistoga Speedway - Calistoga, CA 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC Western Classic (Dirt) | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 23rd |
|
| 4/6/2014 | Calistoga Speedway - Calistoga, CA 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC Western Classic (Dirt) | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 11th |
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| 4/11/2014 | Kings Speedway - Hanford, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | 6th | - | 12th |
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| 4/12/2014 | Perris Auto Speedway - Perris, CA So Cal Sprint Car Spectacular 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC/CRA Sprints 360 Non-Winged Senior Sprints | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 12th |
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| 4/15/2014 | Western Tech Speedway Park - El Paso, TX 410 Sprints - Winged: World of Outlaws Pro Legends | Results | | Jason Sides (410 Sprints - Winged) | 1st | 2nd | - | 12th |
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| 4/18/2014 | Devil's Bowl Speedway - Mesquite, TX 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 10th |
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| 4/19/2014 | Devil's Bowl Speedway - Mesquite, TX 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
|
| 4/25/2014 | Salina Highbanks Speedway - Salina, OK 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 16th |
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| 4/26/2014 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 12th | - |
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| 5/2/2014 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 18th |
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| 5/3/2014 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 5/10/2014 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 10th |
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| 5/14/2014 | Lincoln Speedway - Abbottstown, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 11th | - |
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| 5/16/2014 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | - | - |
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| 5/17/2014 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 25th |
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| 5/18/2014 | Orange County Fair Speedway - Middletown, NY 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 12th |
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| 5/20/2014 | New Egypt Speedway - New Egypt, NJ 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 20th |
|
| 5/23/2014 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 19th |
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| 5/26/2014 | Lawrenceburg Speedway - Lawrenceburg, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 15th | - |
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| 5/30/2014 | Attica Raceway Park - Attica, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 12th | - | - | - |
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| 5/31/2014 | I-96 Speedway - Lake Odessa, MI 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 14th |
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| 6/6/2014 | I-80 Speedway - Greenwood, NE 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 10th | - | 4th | 13th |
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| 6/7/2014 | Lakeside Speedway - Kansas City, KS 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | - | 15th |
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| 6/13/2014 | Jackson Motorplex - Jackson, MN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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| 6/14/2014 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 5th | - |
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| 6/20/2014 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws with Northern Outlaw Sprint Association | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 9th |
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| 6/21/2014 | I-94 Speedway - Fergus Falls, MN 410 Sprints - Winged: World of Outlaws with Northern Outlaw Sprint Association | Results | | Jason Sides (410 Sprints - Winged) | 4th | 4th | - | 11th |
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| 6/27/2014 | 34 Raceway - West Burlington, IA 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 12th |
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| 6/28/2014 | Beaver Dam Raceway - Beaver Dam, WI 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | 13th |
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| 6/29/2014 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 15th |
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| 7/2/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged: World of Outlaws Winged Outlaw, Winged A-Class, Street Stocks | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 2nd | 16th |
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| 7/4/2014 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | 4th | - | 5th |
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| 7/5/2014 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 7/9/2014 | Limaland Motorsports Park - Lima, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 14th |
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| 7/11/2014 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders 410 Sprints - Winged: World of Outlaws with All Star Circuit of Champions | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 7th | 19th |
|
| 7/12/2014 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders 410 Sprints - Winged: World of Outlaws with All Star Circuit of Champions | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 10th |
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| 7/15/2014 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | 7th | - | 7th |
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| 7/17/2014 | Lincoln Speedway - Abbottstown, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 10th | - | 19th | - |
|
| 7/18/2014 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | - | - |
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| 7/19/2014 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 10th | - | 16th | - |
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| 7/20/2014 | Lebanon Valley Speedway - West Lebanon, NY 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 7/23/2014 | Fulton Speedway - Fulton, NY 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | 7th | - | 10th |
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| 7/26/2014 | Autodrome Drummond - Drummondville, QC 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 10th |
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| 7/27/2014 | Cornwall Motor Speedway - Cornwall, ON 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 15th |
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| 7/29/2014 | Ohsweken Speedway - Ohsweken, ON 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Pure Stock | Results | | Jason Sides (410 Sprints - Winged) | 4th | 8th | - | 19th |
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| 8/1/2014 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 16th |
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| 8/2/2014 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 14th |
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| 8/6/2014 | Knoxville Raceway - Knoxville, IA NIGHT #1 OF 410 NATIONALS 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 23rd | - |
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| 8/8/2014 | Knoxville Raceway - Knoxville, IA NIGHT #3 OF 410 NATIONALS 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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| 8/9/2014 | Knoxville Raceway - Knoxville, IA NIGHT #4 OF 410 NATIONALS 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 8/12/2014 | Junction Motor Speedway - McCool Junction, NE 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 10th |
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| 8/15/2014 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 15th |
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| 8/17/2014 | Nodak Speedway - Minot, ND 410 Sprints - Winged: World of Outlaws with Northern Outlaw Sprint Association | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 10th |
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| 8/22/2014 | Castrol Raceway - Edmonton, AB 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 8/23/2014 | Castrol Raceway - Edmonton, AB 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 9th |
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| 8/29/2014 | Skagit Speedway - Burlington, WA 410 Sprints - Winged: World of Outlaws A Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 8th |
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| 8/30/2014 | Skagit Speedway - Burlington, WA 410 Sprints - Winged: World of Outlaws Sportsman Sprints, A Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 8th |
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| 9/1/2014 | Grays Harbor Raceway - Elma, WA STP WORLD OF OUTLAWS Sprint Car Series 410 Sprints - Winged: World of Outlaws A Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 18th |
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| 9/2/2014 | Willamette Speedway - Lebanon, OR WORLD OF OUTLAWS - "SALUTE TO THE KING" 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 8th |
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| 9/3/2014 | ZZZ Southern Oregon Speedway - Medford, OR 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | 6th | - | 6th |
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| 9/5/2014 | Silver Dollar Speedway - Chico, CA Gold Cup Race of Champions 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | - | - |
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| 9/6/2014 | Silver Dollar Speedway - Chico, CA Gold Cup Race of Champions 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 12th |
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| 9/7/2014 | Antioch Speedway - Antioch, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 3rd | 17th |
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| 9/12/2014 | Clay County Fairgrounds - Spencer, IA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 9/13/2014 | Deer Creek Speedway - Spring Valley, MN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 4th | 23rd |
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| 9/16/2014 | Kokomo Speedway - Kokomo, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 14th |
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| 9/17/2014 | Terre Haute Action Track - Terre Haute, IN 410 Sprints - Winged: World of Outlaws Midgets | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | 10th |
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| 9/19/2014 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws Midgets | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 7th | 16th |
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| 9/20/2014 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 16th |
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| 9/26/2014 | Bloomington Speedway - Bloomington, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 9th |
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| 9/27/2014 | Berlin Raceway - Marne, MI 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 11th |
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| 10/4/2014 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | - | 22nd |
|
| 10/11/2014 | Rolling Wheels Raceway - Elbridge, NY 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 10/18/2014 | Fremont Speedway - Fremont, OH 410 Sprints - Winged: World of Outlaws Dirt Late Models | Results | | Jason Sides (410 Sprints - Winged) | 1st | 7th | - | 4th |
|
| 10/25/2014 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 11th | - |
|
| 11/6/2014 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Midgets | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
|
| 11/7/2014 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 4th | 24th |
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| 11/8/2014 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | 1st | 7th | - | 14th |
|