Sidekick Boxing

Top 5 Greatest triologies in boxing : Pt.1 Bowe vs Holyfield

Boxing has always been more than just a sport. Its drama, rivalry, emotion and legacy packed into every punch. And nothing captures that spirit better than a triology.

When two fighters step into the ring not once, not twice but three times. It’s no longer just about winning. It becomes about pride, redemption and proving who truly deserves the crown.

Welcome to a special five-part series where we dive deep into the most iconic trilogies in boxing history. These are not just fights — they’re stories of rivalry, redemption, and raw determination. Each article will focus on one legendary matchup, starting with Bowe vs Holyfield, and explore what made these battles unforgettable. Stay tuned as we relive the drama, the build-up, and the legacy left behind in the ring.

Riddick Bowe vs. Evander Holyfield

Evander holyfield had just beaten legends like George Foreman and Larry Holmes, but critics still doubted his credibility in the ring. On the other hand, Riddick Bowe a 25 year old rising star who was undefeated, bigger, younger and meaner- a natural heavyweight trained by Eddie Futch.

When these giants met the first time in November 1992, it instantly became a all time classic. 10th round was legendary as both traded brutal barbs at each other and gave everything in the ring. Ultimately Bowe won the undisputed heavyweight championship by unanimous decision. Riddick Bowe rose as a new giant but Holyfield showed his heart.

Holyfield came with a smarter plan in their second meeting.Bowe entered the ring heavier. Evander Holyfield outboxed the champion and won close majority decision to regain the title. However, the fight is more well known for the “Fan-man”. Where a man crashed into the ring with parachute.

Bowe and Holyfield fought for the final time in 1995. Where Riddick Bowe tko’d Holyfield in the 8th round after surviving early flurries from Holyfield. Riddick Bowe won the triology by 2-1. Holyfield earned respect from boxing world and went onto become one of the most well known faces in 90s boxing. All three fights delivered.

READ MORE: The Different Boxing Title Belts Explained

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