Introduction
Josh Popoola joined Southend United in the summer of 2026 as Kieron Dyer's first signing and arrived with a growing reputation as one of the National League's most exciting young attacking players.
Biography
Popoola began his football journey in the academy system at Watford before later continuing his development with Bournemouth. Like many young players seeking regular senior football, he stepped away from academy football and began building experience in the non-league game.
Career Journey
Watford and Bournemouth
Popoola spent his early years within professional youth systems.
Learning the non-league game
He gained experience at Hitchin Town, Cheshunt and within Stockport County's academy setup, with loans at Spennymoor Town, Chorley and Warrington Town.
Tonbridge and Buxton
Popoola continued his progression with Tonbridge Angels before a productive season with Buxton.
Maidenhead United
His breakthrough season saw him register more than 20 goal contributions and attract interest from several clubs.
Southend United Career
Southend United announced Popoola as Kieron Dyer's first signing in summer 2026. The move reflected the club's desire to add pace, creativity and attacking threat. Dyer described him as a player capable of getting supporters off their seats with his pace, power and skill.
Playing Style
Popoola is a direct attacking player who enjoys running at defenders. His strengths include pace, close control, direct dribbling and creativity in one-v-one situations. While primarily a left winger, he can operate across the front line.
One For The Future
At just 22, Popoola arrives at Southend with much of his career still ahead of him. His performances at Maidenhead demonstrated the quality needed to compete at National League level, but his best years should still be to come.
Key Career Moments
- Developed in the Watford academy
- Continued progression within Bournemouth's youth system
- Gained senior experience with Hitchin Town and Cheshunt
- Joined Stockport County's academy setup
- Completed loan spells with Spennymoor Town, Chorley and Warrington Town
- Played regularly for Tonbridge Angels
- Enjoyed a productive season with Buxton
- Registered more than 20 goal contributions for Maidenhead United
- Won Maidenhead United Goal of the Month in December 2025
- Became Kieron Dyer's first Southend United signing
- Joined Southend United in summer 2026