The 25-year-old was at White Hart Lane as a trainee and young professional for five years between 1994-1999.
After unlucky, injury-hit spells at Leyton Orient and Chester, Castle Bar-born Simon has enjoyed an upturn in fortunes since returning home.
He has lifted two Eircom League titles, one cup and played in the Champions League for what he describes as a 'very forward-thinking club'.
Bohemians were crowned champions in November last year and will kick-off their preparations for the coming season - running from April-November - with tomorrow's sold-out friendly.
"We're all looking forward to it and we'll be up for it," said Simon. "And, of course, it will mean that little more to me.
"There are not that many lads still at the club from my time there.
"Teddy Sheringham is back at Spurs and it will be nice to see him again. I remember the last time I played against Teddy - it was for the youth team against the first team in a training ground match on a Friday.
"It's a great chance for us to play a Premiership team and it's not every day you get that chance, so we'll look to make the most of it."
Simon believes the standard of the Eircom League is on a par with the Second Division of the Nationwide League.
"It's always a tricky one," he said. "In recent years, because there are a few more foreign players in England, a few of the Irish boys have come back and they have the benefit of full-time training and and are very hungry.
"They have so much ability but never quite got that chance.
"I would say the league very much has a full-time mentality but it's hard to compare with English football.
"We are certainly a forward-thinking club, full-time and things are getting better and better all the time. We've got one of the most enthusiastic managers around in Stephen Kenny and he wants to make us the Rosenborg of Ireland.
"We've also got Liam O'Brien, a great midfield who played for Manchester United, Newcastle and Ireland. It's a good place to be at the moment."
Bohemians defender and ex-Spur Simon Webb admits Tuesday's friendly will probably mean that little more to him than anyone else at Dalymount Park.