Aaron joined Rushden & Diamonds Youth Development at the age of 11, moving into the Centre of Excellence in his Under 13 year, where he has continued through to Under 16 level. After his progress in the Diamonds development system he was scouted by Liverpool, and after a successful trial with the Reds he was offered a two-year scholarship with the Reds, signing for them in June 2009.

Aaron began his scholarship on 6th July 2009, becoming the third player in the last two seasons to move from Rushden & Diamonds Youth System to a Premiership club.

Head of Youth Paul Driver commented at the time "We are all absolutely thrilled for Aaron - this is a brilliant achievement for everyone involved in his development throughout the five years that he has been with us.

"His progress with us to get to the level where one of the 'Big 4 Clubs' is prepared to offer him a scholarship also serves as further evidence of how well we have maintained our system despite the withdrawal of financial support from the football authorities in the past two seasons".

During his time in the North-West he struggled with injury, and rejoined the Diamonds in October 2010 - aged 17.

On 12th October 2010 he made his first appearance at first team level when he played in the Hillier Senior Cup in the 8-0 victory over Daventry United.

He was given a place in the Diamonds First Team squad during November 2010, and made his first appearance in the Blue Square Bet Premier as a substitute in the game at Luton Town on 1st January 2011.

Towards the end of January 2011 he went on a Work Experience Loan to Barton Rovers of the Zamaretto League Midland Division.