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#5. Josh Koscheck - 5 fights
UFC record: 15-10-0
Overall record: 17-11-0
With just two professional fights to his name before heading in to the first season of The Ultimate Fighter, Josh "Kos" Koscheck went on to spend almost his entire career with the UFC.
Prior to embarking on the disappointing run which would see him leave the promotion, Koscheck was 15-5-0 with the UFC, an impressive record by anyone's measure. Wins over Diego Sanchez, Anthony Johnson, Paul Daley and Matt Hughes only serve to prove the level of talent "Kos" possessed.
Unfortunately for Koscheck, his drive to fight the best in the division ultimately served to facilitate his downfall as he embarked on a run which saw him face a string of top contenders in quick succession. It all began in May 2012 with an extremely close split decision loss to Johnny Hendricks. Next, Koscheck faced future welterweight champion "Ruthless" Robbie Lawler who was true to his name, ruthlessly dispatching "Kos" via first round KO. A second first round knockout followed in November 2013 at the hands of another future 170lb champion, Tyron Woodley. After taking some much needed time off following the pair of KO losses, Koscheck returned to face Jake Ellenberger at UFC 184 in February 2015, this time losing via submission in the second round. With his losing streak now sitting at four fights, "Kos" took a risky, short notice bout against Erick Silva just 21 days later in the hope of getting back into the win column. Unfortunately for Koscheck, things did not go to plan, with Silva claiming the victory via first round guillotine choke for his fifth consecutive loss in what would turn out to be his final UFC fight.
A brief appearance for Bellator in 2017 ended in all to familiar fashion with "Kos" losing via first round knockout at the hands of Mauricio Alonso and the 40-year-old announced his retirement from the sport the following year.
#6. BJ Penn - 5 fights
UFC record: 12-11-2
Overall record: 16-12-2
No matter what happens as he approaches the end of his career BJ Penn will go down as one of the all-time greats. The longtime UFC lightweight champion consistently fought the best in the world during his career, including challenging for the welterweight title on more than one occasion.
Things have taken a downward turn for "The Prodigy" in recent years. Without a win since 2010, Penn has put together the worst run of his career with five consecutive losses leading to many fans calling for the 39-year-old to walk away from the sport for good.
Despite that, Penn has been booked to face Ryan Hall at UFC 232 in December, a fight which will either see him snap his losing streak and perhaps end his career on a high note or add yet another disappointing loss to his decorated career and leave him pondering a sad end to life as a professional fighter.
