Boxing’s Biggest Underdog Wins

In truth, upsets do not happen often in boxing. That especially holds when prospects are concerned, as managers look to bring up talents slowly, picking their potential cash cow’s fights very carefully. And while many think Buster Douglas beating Mike Tyson at the Tokyo Superdome is the biggest underdog win in pugilism (42 to 1), that is not the case. Here, we tell you about the five boxing bouts that most made sportsbooks dizzy and lined the pockets of savvy gamblers who recognized something few could.

Evan Holyfield vs. Jurmain McDonald

Evander Holyfield is one of the most celebrated boxers of the 1980s and 1990s. He competed professionally for twenty-seven years and won undisputed championships in two weight classes. Nicknamed the Real Deal, Holyfield beat Hall of Famers such as Mike Tyson, Ray Mercer, Riddick Bowe, Michael Moorer, Larry Holmes, and George Foreman. Hence, his place in boxing history cannot get questioned. However, while everyone in combat sports knows who Evander is, few have heard of his son, Evan Holyfield.

Born in 1997, Evan is the middle child of Evander’s eleven, and he made his pro boxing debut in late 2019, beating Nick Winstead by TKO sixteen seconds into the first round in the MGM Grand Garden Arena. Evan followed up this victory with eight more, six of which came by stoppage. In May 2022, he faced Jurmain McDoland, an unknown 6-5 fighter from Jefferson City, at the Kia Forum in Inglewood, California, on a Triller Card. Bookmakers favored Holyfield by as much as 75 to 1.

Yet, to everyone’s shock, Evander Holyfield’s son got KO’d one minute into the second round.

Karol Itauma vs. Ezequiel Maderna

Karol Itauma is a light-heavyweight boxer from Great Britain of Nigerian and Slovak descent. He is the brother of super heavyweight Moses Itauma, who at the time of writing boasted a 20-0 record. Karol won a gold medal at the 2018 Youth Olympics, representing Britain, defeating Ruslan Kolesnikov from Russia 4-1 in the competition’s final. Born in Kezmarok, Slovakia, the Itauma family moved to England, Kent, specifically, when Karol was young, and he signed his first professional contract in England at the age of twenty. He made his debut in December 2020 against Lewis Van Poetsch, winning on points in a four-round fight.

Many pundits expected big things from the young Karol Itauma, who had amassed a 9-0 record coming into Wembley Arena to fight for the vacant WBC International light-heavyweight title against Ezequiel Maderna. Maderna, a respectable boxer with a record of 31-11, was coming off a KO loss to Fedor Chudinov and was thirty-six at the time of the contest, considered at the end of his career. Many assumed he was just a body for Karol to beat en route to capturing his first major title. Bookies saw Itauma as a 66 to 1 favorite, but he did not manage to live up to their expectations, as he suffered a TKO loss at the hands of Maderna in the fifth round of their Wembley Arena bout.

Kanat Islam vs. Jimmy Kelly

Chinese-born Kazakhstani Kanat Islam is a 2008 Summer Olympics (Beijing) bronze medalist who also took third in the 2007 World Amateur Championships, the 2007 Asian Championships, and the 2006 Asian Games. Kanat turned pro in 2012, beating Daniel Beato by KO in the third round in a fight that happened in the Dominican Republic, the country where he fought for a large part of the initial section of his professional run.

In 2016, Kanat won the vacant WBO Inter-Continental light-middleweight title against Patrick Allotey. In February of 2022, he entered the ring to compete against Britain’s Jimmy Kelly for the WBO global middleweight title, with a record of 28-0. Sportsbooks considered him a 50 to 1 favorite, and he stunned experts, fans, and gambling sites by losing to the 27-2 Kelly from Manchester by majority decision on scorecards of 95-95, 96-94, and 97-93.

Vito Mielnicki Jr. vs. James Martin

Here is another example of a 50 to 1 favorite dropping the ball. Called White Magic, Vito Mielnicki Jr. is a four-time Junior National Golden Gloves champion. This Belleville native turned pro right after high school, and nineteen months into his career, he had an 8-0 record with five stoppages. Looked at as a future title contender at welterweight, no one expected that the 6-2 James Martin would even give Mielnicki Jr. any problems. Nonetheless, things took an unexpected turn, as the rising prospect from New Jersey got outboxed to an eight-round majority decision by the unheralded kid from Philadelphia at Shrine Auditorium & Expo Hall in Los Angeles in a junior middleweight bout.

After incurring his first pro career blemish, Melnicki managed to bounce back into contention, winning ten straight until we posted this article and capturing the WBC Youth light middleweight title in November 2023.

Kurt Scoby vs. Dakota Linger

Kurt Scoby made the news cycle as a former football prospect who turned to boxing as a way not to squander his athletic talents. Scoby grew up in Duarte, California, surrounded by gang violence, and saw boxing as his way out of a bad living situation. He got scouted by the Chargers and Steelers as a Fresno State University running back but did not get offered an NFL contract. Still, his physical abilities were never in doubt, and they seemed to translate well into the Sweet Science.

Fighting out of New York, Scoby met Dakota Linger at the Overtime Elite Arena in April 2024 as a 50 to 1 favorite for a featherweight contest. Scoby came into the fight with thirteen wins and no losses to his name, eleven of which he earned by stoppage. Linger made the walk in the Overtime Elite Arena with a record of thirteen wins also but listed six losses, three by KO. Inside the ring, records do not fight, and Linger stopped Scoby by TKO in the sixth round out of a scheduled eight, putting a bump in the rod to Scoby’s contender aspirations.

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