Winner was born in St. George's, Grenada to a British father and an Afro-Caribbean mother, and moved to Leicester, United Kingdom at seven years old. Winner is one of three brothers and is the middle child. His older brother is William and his younger brother is named Michael. Michael is often in his corner during his fights and often assists in training. He started in sports during his high school years, competing in football and other athletics. Winner never thought of being a mixed martial artist but loved sports. He went to self-defense classes at Leicester Shootfighters and met Dan Hardy and Paul Daley. Hardy inspired Winner to give the sport a real try.
Winner tried out for the eighth season of the Ultimate Fighter. He did not make the cut but tried out for the ninth season and made the show.
To get into The Ultimate Fighter house, Winner fought Gary Kelly. Winner won by knockout while working Kelly in the clinch. Winner then flew to Las Vegas to compete under coach Michael Bisping against the US team. He advanced to the semifinals of the lightweight tournament after defeating Santino Defranco by TKO in the first round. Winner then had his last fight on the show defeating Cameron Dollar by submission in round one. The win over Dollar put Winner in the finals to fight teammate, Ross Pearson.
Winner fought Ross Pearson at The Ultimate Finale 9 in Las Vegas, Nevada. Winner lost by unanimous decision, along with losing the six-figure contract.
He defeated Rolando Delgado via first round KO on 14 November 2009, at UFC 105.
Winner was scheduled to face Cole Miller on 31 March 2010 at UFC Fight Night 21. However, Miller was forced off the card after suffering an injury. Rafaello Oliveira was later confirmed as his replacement. Winner won via unanimous decision.
At UFC 118, Winner's fight was selected to be a part of the SpikeTV broadcast. He fought Nik Lentz, losing via unanimous decision after being out wrestled for all three rounds.
Winner then faced Dennis Siver on 13 November 2010 at UFC 122. He lost the fight via submission in the first round.
Winner lost to Anthony Njokuani on 2 July 2011 at UFC 132 via unanimous decision. Following the loss, Winner was released from the promotion.
Winner recently signed a contract with British promotion BAMMA. His first fight on was at BAMMA 7 against BAMMA veteran Jason Ball. Winner won the fight via unanimous decision.
Winner next competed in a Lightweight Title Eliminator bout against Diego Gonzalez at BAMMA 8. He again won via unanimous decision.
Winner next faced Rob Sinclair for the BAMMA Lightweight title at BAMMA 10, the first MMA event to be shown on Channel 5. Winner lost the fight via split decision.
On 3 May 2014 Winner fought in a 7-man tournament at All or Nothing 6. Winner won his quarter final fight via TKO against Jordan Miller before winning a decision victory against Stephen Martin. In the final, Winner defeated Artem Lobov via unanimous decision and therefore won the overall tournament.
At KSW 24, Winner challenged Mateusz Gamrot in a lightweight bout. He lost the fight via unanimous decision.
Winner faced to Akop Stepanyan on 29 August 2015 at League S-70: Russia vs. World. He lost via unanimous decision.