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Leonard joined Blues after impressing on trial before the start of the 2011/12 season and went on to make 23 appearances in his first year at the club.
Leonard, who worked with former boss Paul Sturrock at Plymouth Argyle before joining Blues has been one of Blues’ standout performers in recent seasons, winning the admiration of the fans – picking up two Supporters’ Player of the Season Awards in 2013-14 and 2015-16.
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.
He is now a key figure in Southend’s midfield, having racked up over 200 appearances at the club.