In his next fight, Barkley lost his title via split decision in a 12-round war with Roberto Durán, in a fight proclaimed 1989 Fight of the Year by "Ring" magazine. Following the defeat to Duran, Barkley took on undefeated Michael Nunn for the IBF and lineal middleweight titles, dropping a close majority decision. He next fought Nigel Benn in a challenge for the WBO middleweight title and was stopped on the three-knockdown rule at the end of a wild first round in which both fighters were hurt.