#2. Darren Till - UFC middleweight
Darren Till came into the UFC with a perfect 12-0 and went unbeaten in his first four octagon bouts to earn his first main event against Donald 'Cowboy' Cerrone. He won that bout via TKO and went on to defeat Stephen 'Wonderboy' Thompson in another main event to earn a welterweight title opportunity.
That bout was a PPV main event against the champion Tyron Woodley, which he lost via submission. He's competed in three main events since, all were losing efforts, against Jorge Masvidal, Robert Whittaker, and Derek Brunson. The latter two coming after he moved up in weight class to middleweight.
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Having lost two straight and four of his last five, Till's next bout will be a very important one for his career. While things may not be looking great at the moment, he's still only 29 years old and could very well turn things around before all is said and done.
#1. Michael Bisping - former UFC middleweight
Michael Bisping entered the promotion off the back of winning season three of The Ultimate Fighter. After winning that competition, Bisping had to go through 13 bouts inside the octagon to get his first main event. He got his first headline bout against Jason Miller and won the fight via TKO.
Bisping would then lose three of his next four main events, dropping results to Vitor Belfort, Tim Kennedy, and Luke Rockhold. However, he then went on a winning spree in headline bouts, including wins over Anderson Silva and then a title-winning performance against Rockhold.
Bisping would then successfully defend his title against Dan Henderson to earn himself a super-fight against Georges St-Pierre. He lost that bout and was forced to retire after another loss to Kelvin Gastelum. However, his legacy is secure as the first UK fighter ever to win UFC gold.