[2] On July 4, 2007, Chestnut won the 92nd Annual Nathan's Hot Dog Eating Contest held at New York City.

That same year, during Nathan's Hot Dog Eating Contest, he ate 32 HDB, placing third behind Takeru Kobayashi and Sonya Thomas.

[18] Chestnut lost to Kobayashi in the Johnsonville World Bratwurst Eating Championship in Sheboygan, Wisconsin.

[19] In 2007, Chestnut won the Wing Bowl XV, an annual Philadelphia event at the Wachovia Center.

[25] On March 24, 2008, Chestnut set a new male record at The Big Texan Steak Ranch restaurant in Amarillo, Texas, by eating a meal of 4.5 lb (2.04 kg) ribeye steak, salad, baked potato, shrimp cocktail, and roll in just eight minutes and 52 seconds.

Shortly afterwards, on his show on KKLA, previous record holder Frank Pastore congratulated Chestnut.

)[26] On June 21, 2008, Chestnut lost to Takeru Kobayashi in a Pizza Hut P'Zone competition at Sony Studios in Culver City, California.

On July 4, 2008, Chestnut tied Takeru Kobayashi in the annual Nathan's Hot Dog Contest after eating 59 HDB in ten minutes.

[27] On July 28, 2008, Chestnut lost to Takeru Kobayashi in Chicken Satay eating in the MLE Asia inaugural event.

[28] On February 21, 2009, Chestnut consumed 10.5 lb (4.8 kg) of macaroni and cheese in seven minutes during halftime at the San Jose Stealth lacrosse game, beating out his contestants and adding another world record to his name.

[30] On September 27, 2009, Chestnut lost to Takeru Kobayashi in Krystal Square Off World Hamburger Eating Championship.

[31] On Man v. Food in San Jose, California, Chestnut ate Iguana's Burritozilla: a five lb (2.3 kg), 17-inch burrito in three minutes, ten seconds.

[32] On July 4, 2010, Chestnut secured his fourth straight Nathan's Hotdog Eating Contest, by consuming 54 HDB in what he described himself as a disappointing performance.

On July 4, 2011, Chestnut secured his fifth straight Nathan's Hotdog Eating Contest, by consuming 62 HDB.

Kobayashi, who could not participate in the contest because of his refusal to sign the required contract, ate 69 HDB at an off-site event with independent judges to establish a new world record.

[37] On July 4, 2012, Chestnut successfully defended his title at Nathan's 97th Annual Hot Dog Eating Contest at Coney Island in Brooklyn, New York.

He tied his own world record by swallowing 68 HDB in ten minutes, which earned him his 6th "mustard belt" for this competition.

[38] On July 16, 2012, Chestnut made a guest appearance on the 12th episode of Hell's Kitchen season 10, in which he participated in a wing-eating competition against a few of the contestants.

[42] On July 4, 2013, Chestnut successfully defended his title at Nathan's 98th Annual Hot Dog Eating Contest at Coney Island in Brooklyn, New York.

He beat his own world record of 68 by consuming 69 HDB in ten minutes, which earned him his 7th Mustard Belt for this competition.

[4] On July 25, 2013, Chestnut ate 179 wings in ten minutes taking the title for the second year in a row at the Hooters World Wing-Eating Championship held in Clearwater, Florida.

[44] On July 4, 2014, Chestnut ate more hot dogs and buns than any of his opponents, narrowly defeating competitor Matt Stonie.

[48] In 2018, Chestnut competed in The Amazing Race 30 alongside fellow competitive eater Tim Janus.

[52] On August 1, 2020, Chestnut ate nine pounds (4.1 kg) of pizza in 32 minutes and 14 seconds in a MrBeast YouTube video in Greenville, North Carolina.

Chestnut won the contest, as the four Army soldiers ate 49 hot dogs all together, with Impossible Foods donating $106,000 to Operation Homefront as a result.