#4. Charles Oliveira - TUF Latin America 3 Finale
Former lightweight champion Charles Oliveira was in a different place back in 2016. The Brazilian was not at the helm of a 11-fight win streak or anywhere close to a title fight. Instead, he was a featherweight with a history of failing to make weight, having failed to make the weight cut four times by then. Looking to bounce back from a submission loss to Anthony Pettis, 'do Bronx' agreed to face Ricardo Lamas.
Their bout was scheduled to take place at The Ultimate Fighter Latin America 3 finale. In his final featherweight bout, Charles Oliveira once again failed to make weight as he was 9 lbs over the featherweight limit. Worse still, Oliveira lost to Lamas due to the very same submission that Pettis used to tap him out, i.e., a guillotine choke.
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On a 2-fight losing streak and clearly too big for the weight class, Oliveira had no choice but to make a lightweight return for his next bout. However, the rest is history.
#3. Kelvin Gastelum - UFC 183
Like many of the fighters on this list, Kelvin Gastelum has a history of weigh-in failures. Standing at 5'9" with a 71.5-inch reach, it is difficult to understand why. However, the former middleweight title challenger seems to struggle the most with his nutrition. Thus far, Gastelum has missed weight twice in his career, which is egregious given that his height and reach are both exceeded by many lightweights.
In 2015, Gastelum was an undefeated fighter whose in-cage tenacity drew comparisons to former heavyweight champion Cain Velasquez. With a perfect 10-0 record, Gastelum was scheduled to face Tyron Woodley at welterweight. However, jaws dropped when the now former welterweight stepped on the scales. He was 10 lbs over the welterweight limit and was forced to forfeit 30% of his fight purse.
Woodley declined to take Gastelum's money before defeating his foe by split-decision. Dana White later forced Gastelum to ply his trade at middleweight as it was his second weigh-in failure and by a margin only exceeded by one other fighter in UFC history.