Kirkland suffered his first loss to Nobuhiro Ishida in April 2011. In November 2011 he defeated Alfredo Angulo to win the WBC Continental Americas Light Middleweight title. Kirkland’s last fight was a loss to Saul Alvarez in May 2015 to bring his record to 32 – 2 with 28 knockouts. He spent 30 months in prison for an armed robbery conviction in 2003. In 2009 he was sentenced to 24 months in prison and plead guilty to a firearm charge. He was arrested again in 2013 for assault.