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UFC legend made his opponent quit with a signature jaw-breaking head kick to earn title shot

On this day in 2015, a legend of the sport cemented himself as the next title challenger in the lightweight division.

When Donald ‘Cowboy’ Cerrone entered the modern wing of the UFC Hall of Fame in 2023, he did it with one of the most impressive highlight reels of any mixed martial artist.

Cerrone may be planning on making a return but his legacy was already assured come 2022 where he laid the gloves down after sharing the Octagon with Jim Miller at UFC 276.

If there’s one strike in particular that ‘Cowboy’ was best known for, it was his signature head kicks that could end the fight in one devastating motion.

One of his very best kicks was delivered on the same night that Daniel Cormier defeated Anthony ‘Rumble’ Johnson to win the vacant light heavyweight title.

Donald Cerrone speaks on stage at the UFC Hall of Fame induction ceremony in 2023
Photo by Chris Unger/Zuffa LLC via Getty Images

Donald ‘Cowboy’ Cerrone broke John Makdessi’s jaw at UFC 187 on this day in 2015

At UFC 187, Donald ‘Cowboy’ Cerrone was set to face the undefeated Khabib Nurmagomedov at the MGM Grand Garden Arena in Las Vegas.

With both men having extensive winning streaks at 155 pounds, it was expected that the winner would go on to face the new champion, Rafael dos Anjos, who both men had history with.

Nurmagomedov withdrew from the fight several weeks out and was replaced by Canada’s John Makdessi who was coming off of a first round finish at UFC 186 the month prior.

Many expected that the fight would be a mismatch and that’s what played out on the main card as Cerrone continued to pick away at his opponent with his superior striking.

In the second round, ‘Cowboy’ unleashed one of his famous head kicks which landed clean, with Makdessi immediately signalling to the referee and his opponent that the fight needed to be stopped.

Jason Herzog waved the fight off with Makdessi later revealing that he had broken his jaw, an injury that kept him out of action for the majority of the year.

Cerrone went on to challenge dos Anjos for the lightweight title in December where the champion retained his title in just over a minute.

UFC 187 would also see a future lightweight champion make his Octagon debut

Along with Donald Cerrone earning the next lightweight title shot, UFC 187 was a highly significant moment for the division for a different reason.

In the second fight of the night, Islam Makhachev would make the walk for the first time, arriving in the promotion with a perfect record of 11-0.

He extended this winning streak by submitting America’s Leo Kuntz in the second round with both men making their Octagon debuts.

Makhachev would return later that year at UFC 192 where he suffered his first and only defeat, being knocked out by Adriano Martins in the first round.