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November 4th, 1989. On this day, one of the most explosive albeit underrated heavyweight bouts took place between 2 undefeated heavyweights; Evander “Real Deal” Holyfield & Alex Stewart aka “The Destroyer”. This is Holyfield’s 5th fight as a heavyweight and the 2nd defense of his WBC Continental Americas Heavyweight Championship.

At this time, Holyfield was also the No. 1 World Heavyweight Contender while Stewart was ranked No. 2 by the WBA.

Prefight records; Holyfield 22(18)-0, Stewart 24(24)-0.

Back in July 1988, Evander Holyfield made his heavyweight debut against former world title challenger James “Quick” Tillis and won via RTD5. Holyfield would go on to garner 3 consecutive stoppage wins from December 1988 to July 1989 before facing undefeated hard punching Brit, Alex Stewart.

Going into the fight, Holyfield was the Undisputed Cruiserweight World Champion and largely regarded as the Greatest Cruiserweight Boxer of All Time. At this juncture of his career, he had beaten notable oppositions such as Ricky Parkey, Carlos De Leon, Tyrone Booze, Henry Tillman, James Tillis, Pinklon Thomas, Michael Dokes, Ossie Ocasio & Dwight Muhammad Qawi (2x).

On the other hand, the 13-1 underdog Alex Stewart did not have any notable victories yet; as he largely fought lower tier competition despite an unblemished pro record. Thus, Stewart’s lack of exposure against quality opposition led many to believe that he would not last more than a few innings against the proven Holyfield.

* Interestingly, Stewart’s perfect record of 24(24)-0 tied with former heavyweight contender Mac Foster who had the same record up till April 1970.Should Stewart beat Holyfield via knockout, he will set an all time American record to surpass Mac Foster. Up to this point, the heavyweight with the most consecutive knockout wins is Jose Manuel Urtain from Spain, at 30(30)-0.

Besides, Stewart had never engaged in a tough fight while Holyfield have had brutal wars against Michael Dokes and Dwight Muhammad Qawi. Moreover, Stewart had never gone beyond 4 rounds.

To the surprise of the boxing world, Stewart put up an impressive performance and pushed Holyfield into an all out war; trading power shots and rocking one another in an exciting, all action affair. Although Stewart lost most of the rounds, but he showed tremendous power, skills & grit against the Real Deal.

Stewart’s best round was in the 5th when he connected with a left-right combination that badly staggered Holyfield and followed up with a barrage of punches. This was the only round won by Stewart in the official scorecards.

But in next stanza, Holyfield returned the favor and badly hurt Stewart; worsening the cut above Stewart’s right eye. Evander’s onslaught lasted for more than half the round but The Destroyer showed grit and made it to the bell.

Stewart’s eye had been cut in the 2nd round but ringside physician Dr. Frank Doggett allowed the fight to go on as it wasn’t affecting his vision. However, after the 6th the cut had become unmanageable. Additionally, Stewart was badly weakened by the accumulation of punishment and fought the next 2 rounds exhausted and without control of his legs.

With 10 seconds left in the 8th frame, Doggett halted the bout as the cut was wide open and Stewart’s face a bloody mess.

In spite of the loss, Stewart earned newfound respect for his courage which Holyfield praised in the post fight interview. He had exceeded the expectations of most, and certainly did not look like a 13-1 underdog with that performance.

Both fighters would collide in a return bout 4 years after.

Hope you guys enjoy this highlight of an underrated heavyweight war and don’t forget to SUBSCRIBE!

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