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TAKE FIVE: A Look Back at the Top Five Races of the 2021 Season | World of Outlaws


A season of wins, losses, heartbreak, and memories is over—culminating in the fourth World of Outlaws Late Models Championship for Brandon Sheppard and eighth for Rocket1 Racing.

The Most Powerful Late Models on the Planet battled 49 times in 2021, producing 21 different winners. Six of them reached Victory Lane for the first time in Series competition, including Bobby Pierce and NASCAR Cup Champion Kyle Larson.

While those 49 races each provided moments to remember, five stood out during the 11-month campaign.

Here are the top five races of the 2021 season:

Sharon Speedway- August 21
Winner: Kyle Larson

A hot August night set the stage for the World of Outlaws Late Models only appearance at Sharon Speedway in 2021.

Sharon Speedway
Ryan Gustin battles Kyle Larson at Sharon Speedway/Jacy Norgaard photo

Kyle Larson led the field to the green of the 40 Lap Feature and dominated the race until the caution came out with 13 laps remaining.

That’s when he met “The Reaper.”

Ryan Gustin powered past Brandon Sheppard to move into second, calculating his move on the outside lane to try and catch “Yung Money.”

The Marshalltown, IA driver pulled even with Larson in the closing laps of the race, but the 2021 NASCAR Cup Series Champion held him at bay for his second World of Outlaws Late Models Victory of the season—in only his third appearance.

Highlights: https://bit.ly/30vwZWq

4. Orange County Fair Speedway- August 19
Winner: Brandon Sheppard

The World of Outlaws Late Models made their first appearance at the Orange County Fair Speedway since 2004 in August, and the battle for Empire State glory didn’t disappoint.

Blair and Sheppard race at OCFS
Brandon Sheppard holds off Max Blair for the win at Orange County Fair Speedway/Jacy Norgaard photo

Brandon Sheppard, Chris Madden, and Max Blair battled for the top spot throughout the entire event before Madden had trouble with two laps to go.

The yellow flag set up an epic finish between Sheppard and Blair, who stayed side-by-side for the rest of the event. Blair made his last-ditch effort, swinging to the inside of Sheppard. But “The Rocket Shepp” held on to grab the checkered flag by inches.

Tyler Bruening also had a run to be remember at the “House of Power.” The Decorah, IA driver, was forced into a backup car after his Drydene Heat Race and drove to third from the tail of the field.

Highlights: https://bit.ly/3kJpB0q

3. Gondik Law Speedway- July 13
Winner: Brandon Sheppard

The World of Outlaws made their annual Northern swing in July, including a stop on the banks of Lake Superior.

Veteran Late Model campaigner Dennis Erb Jr. took the lead early in the Feature, holding off challenges from Brandon Sheppard and Chris Madden.

Sheppard and Madden race at Gondik Law
Brandon Sheppard and Chris Madden battle on the last lap at Gondik Law Speedway/Jacy Norgaard photo

Sheppard used the bottom through the race’s first half before a timely switch paid off for the New Berlin, IL driver. He fired around the outside of Erb to take the lead, and it wasn’t long before Madden followed.

The 2021 champion looked to be on his way to another Victory until a yellow put Madden right behind him with two laps to go.

Sheppard went back to the outside line and had momentum over Madden when they took the white flag. That’s when the Gray Court, SC driver caught a head of steam on the inside of the track. Madden pulled even through Turns 3 and 4, but Sheppard’s momentum in Turn 4 was too much as he took his second straight win at Gondik Law Speedway.

Highlights: https://bit.ly/3cpm9TT

2. Farmer City Raceway- April 3
Winner: Bobby Pierce

The 2021 edition of the Illini 100 put Oakwood, IL driver Bobby Pierce on a stage he’d never forget. Entering the 75 Lap finale, the “Smooth Operator” hadn’t won a World of Outlaws Feature.

Pierce distanced himself from Chris Madden early in the race until slower traffic gave “Smokey” a chance. Madden gave it his best shot until Ricky Thornton Jr. took the position away and pursued Pierce.

Pierce leads Dillard at Farmer City
Bobby Pierce holds off Cade Dillard for the win at Farmer City Raceway/Jacy Norgaard photo

Thornton’s chase would last until he broke with five laps to go, setting up an epic finale.

Cade Dillard drove under Pierce on the restart, trying to escape the 32’s clutches. But when the Illini 100 trophy looked like it was going back to Louisiana, Pierce tightened the belts and pulled a slide-job at the White Flag.

Pierce held on for his first World of Outlaws win— a victory he backed up a month later at Boone Speedway.

Highlights: https://bit.ly/322f0ad

1. Mississippi Thunder Speedway- May 8
Winner: Chris Madden

The World of Outlaws Late Models made their first appearance at Mississippi Thunder in May, and the action didn’t disappoint. Chris Madden led most of the 60 lap Feature on May 8, but it wasn’t without spectacular racing behind him.

Brandon Sheppard, Kyle Strickler, Ryan Gustin, Jimmy Mars, and Bobby Pierce all traded positions throughout the event, but all eyes were on Strickler and Sheppard.

The two drivers fought tooth and nail, throwing slide job after slide job at each other throughout the event. Sheppard ended up with a third-place finish, while Strickler finished fourth.

Neither them nor Gustin could catch Madden on this night, as “Smokey” brought home the $22,500 prize for his then second win of 2021.

Highlights: https://bit.ly/3x8MJKV

The World of Outlaws Late Models is full speed toward 2022—a campaign taking them to 34 tracks in 16 different states.

READ MORE: 2022 SCHEDULE: WORLD OF OUTLAWS LATE MODELS PREPARE FOR JAM-PACKED CAMPAIGN THROUGH 16 STATES

The action kicks off January 20-22 when The Most Powerful Late Models on the Planet head to Volusia Speedway Park in Barberville, FL, for Sunshine Nationals. For Tickets: CLICK HERE.

If you can’t make it to the event, the entire 2022 season will be live on DIRTVision – available either online or through the DIRTVision App.



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