Ryan Leonard joined Blues after impressing on trial before the start of the 2011-12 season. He worked with former boss Paul Sturrock at Plymouth Argyle before joining Blues and has gone onto become one of Blues’ standout performers in his time at the club. In his six years, Leonard has won the admiration of the fans to scoop three Supporters’ Player of the Season Awards; 2013/14, 2015/16 and 2016/17. He is only the second player behind Ronnie Pountney to do so. The central-midfielder also picked up Southend United’s Goal of the Season gong in 2015/16 for his unstoppable strike at Sheffield United in November 2015, repeating the feat again in 2016/17 with his goal against Oxford United in a 2-1 win. He is now a key figure in Southend’s midfield, having racked up over 250 appearances at the club. In January 2018, Sheffield United signed Ryan Leonard on a three-and-a-half-year deal for an undisclosed fee. Ryan made 13 appearances for United.
In August 2018 Ryan left Bramall Lane to join Millwall on-loan, in a move that became a permanent transfer in January 2019.