Simon Milton scored three goals in two games for Exeter City when on loan from Ipswich Town in 1987/88. Having a similar spell with Torquay United shortly afterwards, he returned to Portman Road and soon established himself on the way to making over 300 league and cup 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, Simon moved to Thetford in Norfolk as a teenager and began his junior career with Thetford Rovers. He had unsuccessful trials with Norwich City and Cambridge United before making senior appearances for Thetford and Bury Town. Impressing for Bury in a friendly against Ipswich Town, he eventually moved to Portman Road in a £5,000 transfer. 

Loaned to Exeter City in November 1987 to gain experience, Simon netted both goals on his debut in a 2-1 over Stockport County followed by another strike at Darlington in the following game. 

Having another loan spell with Torquay United (one goal in four matches), Simon’s career at Ipswich took off as he went on to make 332 league and cup appearances scoring 55 goals. The club’s player of the year in 1996, he subsequently had a short spell with Braintree Town before returning to Ipswich to join the academy coaching staff and serve the club in various capacities until 2017.