5 Defining Moments: Kevin Holland

Kevin Holland has now spent more than half of his professional career in the Ultimate Fighting Championship—a reality that would likely have been thought impossible after he made his organizational debut four-plus years ago.

The “Trailblazer” will look to get back on track when he confronts American Top Team’s Santiago Ponzinibbio in a UFC 287 welterweight attraction on Saturday at Miami-Dade Arena in Miami. Holland heads into the match on the heels of back-to-back losses. His record inside the Octagon having fallen to 10-6 with one no contest, he has not posted a victory since he took care of Tim Means with a brabo choke at UFC on ESPN 37 in June.

As Holland approaches his confrontation with Ponzinibbio at 170 pounds, a look at five of the many moments that have come to define him:

1. A Mark of Legitimacy

Holland captured the Xtreme Knockout middleweight championship and did so in decisive fashion when he struck Jose Alfredo Leija into submission in the first round of the XKO 33 headliner on Nov. 5, 2016 at Gas Monkey Live in Dallas. Leija checked out 4:03 into Round 1. Holland overwhelmed his counterpart physically and tactically. He engaged Leija in the clinch and fired knees to the body and legs before a referee restart sent him back into open space. Holland later drove the off-balance Texan to the canvas with a stiff right hand, moved into full mount and unloaded with punches to force the tapout.

2. Speed Bump

Leaning on a combination of guile and brute force, Thiago Santos took a unanimous decision from Holland in their UFC 227 middleweight showcase on Aug. 4, 2018 at the Staples Center in Los Angeles. Scores were 29-27, 29-27 and 29-26. Santos navigated some considerable difficulty in the second round, fought through fatigue, tore into the promotional newcomer with kicks and kept him off-balance with takedowns, ground-and-pound and a few attempted arm-triangle chokes. By the time their 15 minutes in the cage were up, the Brazilian connected with 69 significant strikes to Holland’s 31, completed three takedowns and piled up more than nine minutes of control time.

3. Stepping Over a Legend

Holland punched out two-time Abu Dhabi Combat Club Submission Wrestling World Championships gold medalist Ronaldo Souza in the first round of their UFC 256 middleweight feature on Dec. 12, 2020 at the UFC Apex in Las Vegas. Souza met his end 1:45 into Round 1. Holland remained calm under duress after being taken down by the former Strikeforce champion. He initially threatened Souza with a triangle and elbows from his back, returned to an upright position and made a pass at a guillotine choke. After relinquishing his grip on the Brazilian’s neck, Holland lured him into a kneeling position and unleashed a series of right hands—first from his back, then while seated—that left “Jacare” dazed and defenseless against the cage. Sensing the end was near, he continued to fire punches as he returned to his feet and battered Souza until he was bent over backwards and unconscious.

4. No Forward Progress

Derek Brunson on March 20, 2021 executed takedowns in four of the five rounds, accrued copious amounts of control time, applied his ground-and-pound and ignored the interminable trash talk when he was awarded a unanimous verdict over Holland in the UFC on ESPN 21 main event at the UFC Apex in Las Vegas. Scores were 49-45, 49-46 and 49-46. Holland was effective while he remained upright. However, Brunson withstood his bursts of violence and used his aggression against him, closing the distance to either clinch or pursue takedowns. Holland did what he could to hide his frustration, but his deficit grew with each passing round. He opened a cut near Brunson’s right eye in the fifth round and even recorded a takedown of his own. Success was short-lived and empty. Brunson returned to his feet, secured his final takedown with a little more than a minute left in the match and chewed up the remaining time. The defeat snapped a fight-fight winning streak for Holland and established a clear ceiling for the “Trailblazer” within the Ultimate Fighting Championship’s middleweight division.

5. Signs and Wonders

Stephen Thompson on Dec. 3, 2022 weathered brushes with adversity, kept his head above water and maintained his position as one of the Ultimate Fighting Championship’s premier welterweights when he forced a corner stoppage against Holland in their UFC on ESPN 42 headliner at the Amway Center in Orlando, Florida. It was waved off between the fourth and fifth rounds. In a “Fight of the Year” contender, Holland made the first significant move when he staggered the South Carolinian with an overhand right in the first round and followed up with knee strikes and standing elbows. Thompson recovered, seized the reins in Round 2 and never looked back. He managed distance beautifully, darted into range with punches and cut loose with a dazzling array of leg attacks, from hook kicks and wheel kicks to everything in between. Holland fired back but suffered an apparent hand injury along the way, curtailing some of his effectiveness. Thompson punctuated his performance with a sensational fourth round. There, he increased the frequency and intensity of his kicks, a pair of shots to the liver taking away whatever steam Holland had left. The “Trailblazer” was on the brink of being finished on multiple occasions during the period, and not long after he returned to his corner, the decision was made to shut him down.