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#4. Benson Henderson vs. Anthony Pettis
Benson Henderson fought Anthony Pettis on two occasions, but only one of those bouts came under the UFC banner. Their first fight took place at WEC 53, which Pettis won to claim the lightweight championship.
That fight featured the famous 'Showtime Kick', which is one of the most viral moments in MMA history.
Just over two-and-a-half years later, the pair met once again in a bout for Henderson's UFC lightweight championship. Pettis won via first-round submission and appeared set for super-stardom in the MMA world.
Ultimately, Pettis's run with the belt was somewhat shortlived with only one successful title defense. He then fought for years in the UFC's featherweight, lightweight and welterweight divisions before signing with the PFL for their 2021 season.
#3. Benson Henderson vs. Donald Cerrone
As with Anthony Pettis, Benson Henderson fought Donald Cerrone in his WEC days prior to joining the UFC.
Henderson actually fought 'Cowboy' twice for the WEC lightweight championship, winning both. The first bout went to a decision, whilst the second one saw 'Smooth' secure a first-round submission.
The pair competed almost five years later in the UFC. The bout came during Cerrone's best run in the UFC and just 12 days after his win over Myles Jury. Neither man landed a ton of offense in the bout. Ultimately 'Cowboy' earned a controversial decision victory, likely due to a number of successful takedowns.
Cerrone continued his run to a title fight but was ultimately unsuccessful. Since then, he has competed in both the lightweight and welterweight divisions in the UFC and is now scheduled to face Joe Lauzon at the end of April.
