The 25-year-old played under first-team coach Chris, then reserve team manager, in his time at Spurs between 1994-1999.
Since then Simon has joined Eircom League champions Bohemians via Leyton Orient and Chester while Chris has been appointed assistant manager of the Republic of Ireland on a part-time basis - recognition of his work on the training ground and a distinguished international career with Ireland.
"Chris was absolutely brilliant to me," said Simon. "I've only got good things to say about him.
"He was such a help to me both on and off the pitch.
"I'm so happy he's now involved in the Irish international set up.
"He is the most enthusiastic man I've come across in football and he deserves everything he gets.
"He's such a great guy - the proof of that is how he's survived all the changes at Spurs. It just shows great guys can get to the top as well."
Simon Webb, the ex-Spur in the Bohemians ranks in tonight's friendly, has heaped praise on his former coach Chris Hughton.