Overeem fell victim to Werdum's world class submission skills in the second round and was defeated at PRIDE Total Elimination Absolute in 2006.
Since their fist meeting one fighter has went on to submit a legend and the other is the most hyped fighter not competing in the Ultimate Fighting Championship.
BleacherReport.com profiles Werdum's work since his first fight with Overeem and the training home he's found in California.
Since their fist meeting Werdum has seen mixed results with a 6-3 record.
The Brazilian Jiu-Jitsu black belt was defeated by Antonio Rodrigo Nogueira at PRIDE Critical Countdown Absolute in 2006.
However, he would soon rebound with a submission victory over Aleksander Emelianenko which soon earned him a roster spot in the UFC.
Werdum debuted against former UFC heavyweight champion Andrei Arlovski at UFC 70 and dropped a lackluster decision.
"Vai Cavalo" returned to soundly defeat Gabriel Gonzaga and Brandon Vera by knockout, but an October 2008 knockout loss to Junior Dos Santos would cost Werdum his job in the UFC.
With that being said, the loss to Dos Santos has been his last as Werdum has went on to defeat Mike Kyle, Antonio Silva, and Fedor Emelianenko.
Werdum was a heavy underdog when he faced the former PRIDE heavyweight champion and former pound-for-pound king. But once both gentlemen stepped inside the cage, Werdum shocked the world by defeating Emelianenko with a first-round submission victory.
During Werdum's string of victories, he set up camp with Master Rafael Cordeiro at Kings MMA in California.
Under Cordeiro's tutelage, Werdum's finished two out of three fights under the Strikeforce banner and has shown a vast improvement in his skill-set.
His stable of training partners include former PRIDE champion and UFC middleweight contender Wanderlei Silva, former UFC light-heavyweight champion Mauricio "Shogun" Rua, and UFC middlweight Mark Munoz.
Online sportsbook Bodog.com has Werdum as a +300 underdog leading into Saturday night's fight against Alistair Overeem.
As for whether Werdum can once again shock the world, only time can tell. But one can bet on the fact that he's well prepared and has found a home with Kings MMA.
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