The Most Shocking Boxing Upsets You’ll Never Forget

Boxing has always been unpredictable. No matter how dominant a champion may seem, one punch or one perfect night from an underdog can flip the script and shock the world. Over the years, there have been a handful of fights that not only stunned fans but also changed the course of boxing history. Here are five of the most unforgettable upsets.

Buster Douglas vs Mike Tyson (1990)

When Mike Tyson stepped into the ring in Tokyo, he was the undefeated heavyweight champion and regarded as nearly unbeatable. James “Buster” Douglas entered as a 42-1 underdog, but on that night he delivered the performance of his life. Douglas weathered Tyson’s power, used his jab effectively, and stunned the world with a knockout in the tenth round. It remains one of the biggest surprises in all of sports.

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Hasim Rahman vs Lennox Lewis (2001)

Lennox Lewis was considered the premier heavyweight of his era, but Hasim Rahman had other plans. Fighting in South Africa, Rahman landed a massive right hand in the fifth round that sent Lewis crashing to the canvas. Lewis would eventually win the rematch, but Rahman’s knockout will forever be remembered as a moment when the heavyweight crown briefly slipped into the hands of an unlikely challenger.

Andy Ruiz Jr vs Anthony Joshua (2019)

Anthony Joshua was the undefeated heavyweight champion, known for his size, strength, and technical boxing skills. When Jarrell Miller pulled out, Andy Ruiz Jr stepped in on short notice. Despite being underestimated because of his physique, Ruiz shocked the boxing world by dropping Joshua multiple times and winning by seventh-round TKO. The upset was so stunning that it changed how fans viewed Joshua and proved that appearances can be deceiving.

Corrie Sanders vs Wladimir Klitschko (2003)

Wladimir Klitschko was expected to dominate Corrie Sanders, a South African veteran nearing the end of his career. Instead, Sanders unleashed a lightning-fast assault, knocking Klitschko down multiple times in the second round before scoring a stoppage. The shocking defeat delayed Klitschko’s rise to dominance, though he would later become one of the greatest heavyweights of his era.

Randy Turpin vs Sugar Ray Robinson (1951)

Sugar Ray Robinson is often called the greatest boxer of all time, but even legends can have off nights. Fighting in London, Robinson was expected to easily handle British underdog Randy Turpin. Instead, Turpin outboxed him across 15 rounds to earn a decision victory that left the boxing world stunned. Although Robinson avenged the loss later that year, Turpin’s win remains one of the most iconic upsets in the sport.