Simon Milton played a couple of games for Exeter City when on loan from Ipswich Town in 1987/88. Having a similar spell with Torquay United at around the same time, he returned to Portman Road and soon established himself on the way to making around 280 league appearances for the Suffolk club who he continued to serve in various capacities long after the end of his playing career.Although born in London, Milton moved to Thetford in Norfolk as a teenager and began his career with local side Thetford Rovers. He had unsuccessful trials with Norwich City and Cambridge United and began his senior career with Thetford before joining Bury Town. He played for Thetford in a friendly against Ipswich Town and impressed Ipswich manager Bobby Ferguson enough to earn a trial. Soon after, he was offered a professional contract, but then Ferguson was replaced by John Duncan who honoured the offer and Milton moved to Ipswich from Bury Town for a fee of £5,000. He made his Ipswich debut in December 1987 at Swindon Town.
He was loaned to Exeter City in November 1987 and enjoyed a memorable debut by scoring twice in a 2-1 win at St James’ Park against Stockport County. He followed that up by scoring in the next game at Darlington before returning to Ipswich.
After a similar loan spell with Torquay United where he scored one goal in four matches, his career at Ipswich really took off and he went on to make 332 league appearances for the Portman Road side scoring 55 goals becoming the club's player of the year in 1996. After retiring in 1997, he had a short spell with Braintree Town before returning to Ipswich to join the coaching staff at their academy and continued to serve the club in various capacities until 2017.