5 Defining Moments: Jack Della Maddalena

It could be argued that no one in the Ultimate Fighting Championship welterweight division has more momentum than Jack Della Maddalena.

The ascending Australian contender will look to move another step closer to title contention when he locks horns with Kevin Holland in the UFC Fight Night 227 co-headliner on Saturday at T-Mobile Arena in Las Vegas. Della Maddalena, 27, steps up to the plate on a remarkable 15-fight winning streak that stretches back to 2016. He last appeared at UFC on ESPN 49, where he was awarded a split decision over Elevation Fight Team’s Bassil Hafez on July 15.

As Della Maddalena makes final preparations for his forthcoming battle with Holland at 170 pounds, a look at five of the moments that have helped shape his career to this point:

1. Fork in the Road

Darcy Vendy brushed aside Della Maddalena with a rear-naked choke in the first round of their Eternal MMA 17 middleweight showcase on May 28, 2016 at the Nerang Police-Citizens Youth Club in Nerang, Australia. The end came 4:11 into Round 1. Early back-and-forth exchanges drew blood from Della Maddalena’s nose, and the small cage present for EMMA events made it easier for Vendy to lure him into the clinch. From there, the Shindo New Breed product secured a trip takedown, paid no attention to Della Maddalena’s elbows from the bottom—one of which opened a cut on the scalp—and set up shop in half guard. Vendy then scrambled to the back, secured his position with hooks and cinched the choke. The setback dropped Della Maddalena to 0-2 as a pro and forced him to take inventory at the age of 19. He has not lost since.

2. Boom, Boom, Boom, Out Go the Lights

Della Maddalena captured the Eternal MMA welterweight championship when he punched out Luke Howard in the second round of their EMMA 31 co-main event on March 10, 2018 at the WA Italian Club in Perth, Australia. Referee Diogo Consoni waved it off 28 seconds into Round 2. Della Maddalena established his superiority at the outset and kept his foot on the gas. Body-head combinations flowed freely, along with front kicks to the body and elbows upstairs. Howard completed a brief takedown, only to see it negated, and follow-up attempts were met with stiff resistance. Della Maddalena rolled into full mount under the threat of a kimura, set off a scramble and locked in a standing guillotine at the end of the first round. He pressed forward against the judo black belt at the start of Round 2, ate a clean right hand and reset in open space. Della Maddalena then connected with a left hook to the body, a right uppercut and a crushing left hook to the head that turned out the lights on his countryman.

3. Cashing In

He only needed to see the greener grass on the other side once. Della Maddalena outstruck Kill Cliff Fight Club prospect Ange Loosa to a unanimous decision in a three-round welterweight barnburner during Season 5 of Dana White’s Contender Series on Sept. 14, 2021 at the UFC Apex in Las Vegas. All three cageside judges scored it the same: 30-27 for Della Maddalena, who netted and Ultimate Fighting Championship contract with his performance. The Australian leaned on multi-punch bursts to the body and head, kept Loosa off-balance with stance switches and incorporated occasional knees to the body. Della Maddalena escaped a tight arm-triangle choke from the Titan Fighting Championship alum in the second round, rose to his feet and hacked open a horizontal gash near Loosa’s left eye with a standing elbow strike. Blood seeped and then poured from the wound for the remainder of the match. Della Maddalena fought through fatigue in Round 3, withstood a takedown and closed with a flourish, unleashing with punches, knees and a head kick in the waning seconds.

4. Primetime Player

Della Maddalena put away former M-1 Global champion Ramazan Emeev with punches in the first round of their UFC 275 welterweight attraction on June 12, 2022 at Singapore Indoor Stadium in Kallang, Singapore. Finished for the first time in nearly eight years, Emeev bowed out 2:32 into Round 1. Della Maddalena scrambled out of a takedown, freed himself from an anaconda choke, returned to his feet and went to work with his hands. He pressed Emeev into the fence with punches and cut loose with a pair of left hooks to the body, the second of which forced him to turtle downward in a kneeling, submissive posture. Unanswered punches followed, and referee John Sharp was left no choice but to intervene.

5. No ‘Rude’ Awakening

The former Eternal MMA champion subdued Randy Brown with a rear-naked choke in the first round of their UFC 284 welterweight feature on Feb. 11, 2023 at RAC Arena in Perth, Australia. Della Maddalena drew the curtain 2:13 into Round 1. Brown initially exploited his four-inch height and five-inch reach advantages, keeping the Scrappy MMA rep at a safe distance with a steady jab and routine stance switches. However, Della Maddalena closed in, trapped the onetime Ring of Combat titleholder along the fence and found the mark with a right hook behind the ear. Brown faceplanted onto the canvas, ducked for cover and ate rapid-fired hammerfists until he surrendered his back. Della Maddalena then secured the choke, forced the tap from “Rude Boy” and nailed down his first submission victory in more than five years. The loss closed the book on Brown’s four-fight winning streak.