10 UFC Fighters Who Lost To Surprising Opponents

Dennis "The Menace" Bermudez faced a veritable "who's-who" of opponents in his decade-long professional career. He retired in 2019 at 17-9 and, while he couldn't get it done against the likes of Jeremy Stephens and Chang Sung Jung, among others, he does hold noteworthy victories against the likes of Clay Guida and...Max Holloway?

Yes. That Max Holloway.

At UFC 160 on May 25th, 2013, Holloway and Bermudez squared off on the prelims. While it's difficult to imagine a megastar like Max Holloway on the prelims, it's especially difficult to imagine him losing on said prelims. Nevertheless, Bermudez managed to defeat Holloway via a razor-thin Split Decision, handing him the second loss in his nine-fight career and winning his fourth of an eventual seven straight in the process.

Following the Bermudez loss, Holloway suffered one more defeat at the hands of some nobody named Conor McGregor then went on an absolutely unmitigated tear, winning 13 consecutive fights and capturing Featherweight gold in the process. He's been so good, in fact, that one would be hard-pressed to call him anything other than the greatest of all time in that weight class.

Meanwhile, Bermudez would briefly continue his winning streak, stringing together 3 more wins before losing 2, winning 2 more, losing 4, straight, then calling it a career with a Unanimous Decision win over Te Edwards on a Fight Night card in 2019. While he did end his career on a high note, he never had a victory quite as monumental as the one on this list.