Harry Kyrpainou made his debut for Southend United on Tuesday 30 August 2016 - scoring once in a 2-0 victory over Brighton & Hove Albion

His time at Roots Hall began in September 2015 following a successful trial.

The left-back, who had had previously played for Watford, joined up with Kevin Maher's Under-21 squad and progressed well, helping the side win the Southern Final Third Development League Cup in April 2016.

Kyrprianou made his First Team debut in the Checkatrade Trophy Group Stage fixture v Brighton & Hove Albion, scoring the second goal in a 2-0 victory.

The Cypriot made his league debut in the very next game for the Blues and yet again got on the scoresheet, rifling home a right footed volley against Bolton Wanderers at the Macron Stadium.