Alejandra Guzman fulfilled her vow to serve as the roadblock in Ramla Ali’s title quest.

The former title challenger from Ciudad Obregon, Mexico earned a massive upset win with an eight-round knockout of the iconic Ali. Guzman scored two knockdowns, the latter producing a full ten count at 0:42 of round eight in their DAZN-aired junior featherweight bout Saturday from Smoothie King Center in New Orleans, Louisiana.

Ali had plenty to risk, even as a massive -1800 favorite entering the bout. A victory by the history-making boxer—a Somali refugee who was the nation’s first ever boxer to compete in the Olympics, during the delayed 2020 Tokyo Games—would trigger her first career title shot versus WBC junior featherweight titlist Yamileth Mercado, against whom Guzman lost in her own title bid two fights and three years ago.

None of that convinced the unbeaten rising contender to play it safe, which nearly cost her at several points in the bout and ultimately ended her unbeaten ways.

Ali—who trains out of Manny Robles’ facility in South Gate, California—sat down on her punches, even as Guzman was able to connect with clean right hands in the opening round. Ali showed power of her own, as she landed in combination and was dialed in early with her left hook.

Guzman briefly bucked the knees of Ali with an overhand right late in round three. Ali flashed a world class chin in taking the flush shot, though it was a drastic momentum shift after she controlled the opening two rounds.

Robles urges his charge to box more and not stand toe-to-toe with her aggressive foe. The advice didn’t immediately take and Ali nearly paid the price. Guzman rocked Ali with an overhand right in round four and continued to apply heavy pressure.

Ali boxed well in what appeared to be a big bounce back round in the fifth. That was erased with another right hand by Guzman, which deposited Ali to the canvas for the first time in her career. Ali beat the count and went on to outbox Guzman in round six.

The theme remained the same in the Ali corner. Robles demanded that he continue to ‘box the shit out her’ for the balance of the fight. Ali stuck to the script in round seven, which she began with a crisp one-two and employed subtle in-and-out movement to force Guzman to miss with her counter right.  

Guzman adjusted in round eight to end the fight. After enjoying success with her overhand right, it was a left hook that would end the night. Ali never saw the shot coming as she fell flat on her back. Ali attempted to beat the count but referee Keith Hughes counted her out to produce one of the biggest upsets of 2023.

The loss is the first for Ali (8-1, 2KOs), a human rights and women’s activist and global model who rapidly emerged as a contender to watch in the pros.

Guzman improved to 13-2-2- (7KOs) and is back in position to challenge for a junior featherweight title.

Headlining the show, homegrown favorite Regis Prograis (28-1, 24KOs) will attempt the first defense of his WBC junior welterweight titlist Danielito Zorrilla (17-1, 13KOs).

Jake Donovan is a senior writer for BoxingScene.com. Twitter: @JakeNDaBox