 He spent the remainder of the season on loan at 4th Division Southend United and he was eventually sold to Portsmouth for a fee of £375,000.He won his first of 3 South East Counties Football League Championships whilst still at school with Spurs.After leaving school he joined them as an apprentice winning Best Defender of the Tournament at the prestigious Düsseldorf Football Tournament 2 years on the trot, firstly beating the Russian National Youth Team in the first year and getting knocked out the semi finals in the following.