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The Grueling Truth - Where Legends Speak / The Grueling Truth's Top 10 Sports Lists / Top 10 All-Time Greatest Mexico vs Puerto Rico Fights

Top 10 All-Time Greatest Mexico vs Puerto Rico Fights

Blood battles!
Publish Date: 03/04/2026
Fact checked by: Mark Lewis
Mexico vs Puerto Rico, the greatest fights!

Today’s list is a combination of how historically significant the fight was and how good of a battle it turned out to be.

10. Giovani Segura KO8 Ivan Calderon I

Calderon was only 5’0″ tall and weighed in at 108 pounds. Few boxing champs are smaller than Calderon. However, the diminutive Puerto Rican boxer was not strong enough to defeat Segura. Segura was relentlessly throwing punches. Calderon managed to dodge Segura’s shots for three rounds, but too much time on the ropes led to severe punishment in rounds four to five. Calderon, 35, still had some tricks and boxed through the sixth round before he could not keep up with Segura in the seventh. Calderon’s night ended in round eight with body shots, his first loss as a professional boxer, and his reign’s ended.

Video: Giovanni Segura VS Ivan Calderon 1 (FULL FIGHT)

Giovanni Segura VS Ivan Calderon 1 (FULL FIGHT)

9. Antonio Margarito  TKO11 Miguel Cotto

It was a heated fight until Margarito’s powerful punching turned the tide in the second bout. Round 11 saw a tired and bloodied Cotto retreating. After a Margarito combination, he took a knee and got up. Margarito continued to punish him by continuing to punish him.

Margarito was forced to wrap his hands in the next fight after his opponent noticed a plaster-like appearance. This left some wondering if Margarito’s win over Cotto had been fair and clean.

Video: Miguel Cotto vs Antonio Margarito 1 | FREE FIGHT ON THIS DAY

Miguel Cotto vs Antonio Margarito 1 | FREE FIGHT ON THIS DAY

8. Sixto Escobar KO9 Rodolfo Casanova

Escobar stopped Casanova seventy-seven years before the first Cotto/Margarito fight to possibly lay the foundation for the historical boxing rivalry between these two countries.

It was a close fight. Escobar, a skilled fighter with a vast arsenal and a lot of power, dominated the bout. Escobar won the title of first Puerto Rican to win a world championship.

Casanova was, however, brave in defeat. After suffering his first knockdown in his career, Casanova rose to his feet in Round 3. He continued to fight for the victory until Escobar’s left hook and right uppercut combo at the end of the fight left him utterly beaten to the ground.

Video: SIXTO ESCOBAR TRIBUTE

SIXTO ESCOBAR TRIBUTE

7. Felix Trinidad KO4 Yory Boy Campas

Campas was 56-0 and had 50 knockouts. On the other hand, the Puerto Rican Trinidad was 23-0 with 19 knockouts. After carefully navigating Campas’ left hook in round 1, Trinidad ran straight into it in round 2 and was knocked onto his backside. “Tito,” as he did many times before, tried to get out of trouble but was again rocked in round three. He twice hit Campas low and received a warning, followed by a deduction. Trinidad reacted furiously to the sanction and punished Campas throughout the round and into the fourth until he finally ended the battle.

Video: Felix Tito Trinidad Vs Yory Boy Campas Highlights

Felix Tito Trinidad Vs Yory Boy Campas Highlights

6. Felix Trinidad KO12 Fernando Vargas

Trinidad seemed to be heading for an early win after dropping Vargas twice in Round 1. Vargas fought back and dropped Trinidad in Round 4.

From then on, the fight was bloody carnage as each fighter tried to win. Trinidad knocked Vargas down three more times in Round 12, forcing Jay Nady, the referee, to end the fight. This was a thrilling victory in an epic slugfest.

Video: JEFF JACKSON BOXING HIGHLIGHTS | Felix Trinidad vs Fernando Vargas (TERROR)

JEFF JACKSON BOXING HIGHLIGHTS | Felix Trinidad vs Fernando Vargas (TERROR)

5. Jose Luis Ramirez KO4 Edwin Rosario

In the rematch of their hotly contested first fight a year prior, Ramirez and Rosario put on a show in 1984. Rosario appeared to be on his way to another win. The Puerto Rican looked to add to his close decision victory with a knockout this time, as he floored Ramirez in the first and second rounds.

But Ramirez remained undeterred. He pressed forward, caught Rosario with a right hand in Round 3 and slugged his way to the impressive Round 4 knockout win.

Video: 1984-11-3 Edwin Rosario vs José Luis Ramírez (FOTY)

1984-11-3 Edwin Rosario vs José Luis Ramírez (FOTY)

 

4. Wilfredo Gomes KO5 Carlos Zarate

Gomez fought back against Zarate significantly to defend his junior featherweight title against a long-time bantamweight champion.

Zarate, who was undefeated going into the fight, had won every bout except one by knockout. Gomez proved too much for the Mexican. He was faster and stronger than Zarate, which allowed him to dominate the fight until Round 5, when Harry Gibbs, the referee, stopped it.

Video: Carlos Zarate vs Wilfredo Gomez (Highlights)

Carlos Zarate vs Wilfredo Gomez (Highlights)

3. Wilfredo Gomez TKO14 Lupe Pintor

After defeating Salvador Sanchez, Gomez continued to have extracurricular distractions and a tendency to gain weight between fights. Some wondered if Gomez would be too physically strong for Pintor, and he was, as he used his strength advantage to push the smaller man around in the beginning. Pintor was struggling to adjust after moving from bantamweight to Featherweight. The Mexican finally won the third round. It was a furious, back-and-forth battle. Pintor took Gomez’s ferocious shots. This caused Gomez to lose his composure and sent him to his corner at the end of round 12. A desperate Gomez attacked Pintor and eventually dropped him with a combination that included a body shot. He managed to beat the count but barely and was chased down until he fell again on a left-hand up top. The fight was over right then.

Video: Wilfredo Gomez vs Lupe Pintor : Highlights of the fight

Wilfredo Gomez vs Lupe Pintor : Highlights of the fight

2. Julio Cesar Chavez TKO11 Edwin Rosario

Chavez stated that the world title would go to Mexico before the fight. According to punch stats, Chavez connected with more than 60 per cent of his strikes. Rosario was left gasping for air by many body shots. As Rosario was pinned to the ropes by Chavez, the champion Rosario fought back with about half the amount he ate. Chavez was able to move up a division without difficulty. He absorbed everything and used his strength to push Rosario around. Rosario’s left eye had almost closed by round 10, and his mouth was bloody. His corner saved him the next round by throwing in the towel.

Video: Julio Cesar Chavez vs Edwin Rosario (Highlights)

Julio Cesar Chavez vs Edwin Rosario (Highlights)

1. Salvador Sanchez KO8 Wilfredo Gomez

Although Sanchez had already proven his worth against the likes of Danny “Little Red”, Juan Laporte, and Ruben Castillo, Sanchez was still a 2-to-1 underdog to the charismatic, hard-hitting Puerto Rican, who was rising from 122 to meet the WBC featherweight champion. In the first round, Gomez was the one who landed on the canvas. His bewildered expression suggested that he realized that he was in for a long evening. Sanchez got Gomez into trouble in round two, but he soon relaxed and was content to take out Gomez as a painful lesson of humility. Although his eyes became swollen grotesquely, Bazooka managed to pin Sanchez to the ropes and land bombs now and then. In round eight, the punishment was too harsh for Gomez to continue the fight and “Chava” handed him his first loss. The battle of the bands before the war and the crowd’s atmosphere will never be forgotten.

Video: JEFF JACKSON BOXING HIGHLIGHTS | Salvador Sanchez vs Wilfredo Gomez (LEGENDS)

JEFF JACKSON BOXING HIGHLIGHTS | Salvador Sanchez vs Wilfredo Gomez (LEGENDS)

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