Few fighters in the UFC’s welterweight or middleweight divisions can say they haven’t shared the Octagon with Kevin Holland. The Texas native began his UFC journey back in 2018 under Dana White’s banner, making his debut in the middleweight division with a hard-fought loss to Thiago Santos. Since then, ‘Trailblazer’s path in the world’s premier MMA promotion has been anything but ordinary. The outspoken American has competed 27 times inside the Octagon — surpassing even the great Jon Jones in total UFC appearances since 2008.

In just a few short years, Kevin Holland has built a reputation as one of the busiest and most entertaining fighters on the roster. Known for accepting fights on short notice and taking on anyone the UFC puts in front of him, ‘Trailblazer’ embodies the “anytime, anywhere” spirit that fans love. However, such relentless activity comes at a price. But such an unyielding pace comes with consequences. At one point, Holland admitted he felt like his head was about to pop — almost like a scene straight out of The Boys show. That moment of vulnerability led him to a rare admission: “I want old guys, sorry guys, and easy fights.”

So, what exactly happened to Kevin Holland’s eye?

What caused Kevin Holland’s bloody eyes after UFC 279 fight?

Fighting as often as Kevin Holland does leaves little time for rest — and the threat of serious injury is never far away. The Texas native discovered that the hard way in 2022 when he stepped in against the undefeated Chechen phenom and now middleweight champion, Khamzat Chimaev. Holland was set to face Daniel Rodriguez in a 180-pound catchweight bout at UFC 279, while ‘Borz’ prepared to headline against Nate Diaz at welterweight.

But chaos struck fight week when Khamzat Chimaev missed weight by almost 10 pounds. The UFC scrambled to save the card, ultimately matching ‘Borz’ with Holland in a last-minute reshuffle that stunned fans. What came next turned into one of the most punishing moments of Holland’s career. True to his reputation, Chimaev wasted no time imposing his dominance, submitting Holland with a vicious D’Arce choke in the opening round. The hold squeezed so tightly that it caused ocular bleeding and intense pressure on ‘Trailblazer’s arteries, forcing him to tap.

Since then, Khamzat Chimaev’s vice-like grip has become a trademark of his fighting style. It resurfaced at UFC 308, where his relentless face crank shattered Robert Whittaker’s jaw and displaced several teeth.

Holland claims eye pokes led to broken blood vessels against Khamzat Chimaev

Kevin Holland’s issues with eye injuries long predate his brutal encounter with Khamzat Chimaev. One of his most significant setbacks came in April 2021 against Marvin Vettori. The fight initially favored ‘Trailblazer’ on the feet, as his striking seemed to give him the advantage. But once Vettori realized he couldn’t overpower Holland standing, he brought the fight to the ground, employing relentless control, dominant positioning, and heavy ground-and-pound strikes.

The assault caused severe swelling to Kevin Holland’s left eye, and after a ringside examination, the doctor ruled him unable to continue. However, the ‘Trailblazer’ kept fighting, but in the end, the bout resulted in a loss for the American fighter. Earlier this year, a video of Holland from three years ago resurfaced on social media, reposted by ‘Home of Fight’ on Instagram.

In the clip, the Texas native lies down and discusses an eye poke injury, saying: “Okay, my eyes. Yeah, my eyes are only red because someone was poking them in the fight. Look at that, eye pokes, eye pokes! Look at that, why don’t you guys understand it? There are eye pokes.” It remains unclear whether Holland was referring to his bout with Chimaev, but ‘Home of Fight’ clarified in a postscript that “the video is not after Khamzat fight.”

Tonight, Kevin Holland prepares for his 28th UFC fight in Vancouver, stepping into the co-main event against 33-year-old Mike Malott. Can Malott pose a serious challenge to this seasoned journeyman? Drop your opinion below.