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Tommy joined County as a youngster, having been with Manchester United as a kid, and progressed through County's Centre of Excellence youth system.

Owing to injuries, he was named as a substitute in County's FA Cup 3rd round match at Watford in January 2007, and made his debut when he came on in the 81st minute. Later that season, he played a huge role in the Youth Team's memorable 6-2 Youth League Cup final victory over Colchester United, and finished the season with five first-team appearances under his belt.

Tommy began playing regular first-team football in 2007/08, and scored his first senior goal in the 1-1 draw against Notts County at Edgeley Park. Just three days later, he notched his first hat-trick in a memorable 4-1 victory away to Rotherham United, who were occupying the 3rd and final automatic promotion place at the time.

From that moment onwards he kept his first-team place on the left wing, and scored the only goal of the game in the fantastic 1-0 victory away the Peterborough United, a game which could have seen the Posh promoted themselves, to keep up the momentum in County's own push for promotion.

He went on to play in each Playoff game as County were promoted that season.