After cutting his teeth at a plethora of Premier Youth League teams in Sydney, Simpson made his debut in the NSL with Parramatta Power whilst still a teenager in 2003.
He then secured a contract with Queensland Roar in the inaugural season of the A-League, alongside his twin brother Tyler.
Despite a number of eye catching performances off the bench, Simpson fell out of favour with Miron Bleiberg and was forced to weigh up his options.
?It was frustrating but it?s in the past now,? he said.
?I felt I was playing well at the time but in the end we had a difference of opinion.
?That is the reality of football, some coaches like your style, others have their own methods.
?It was a great experience and I hold no grudges.?
Simpson elected to move abroad and linked with BSC Young Boys in Switzerland in 2006.
Playing alongside the much maligned Ljubo Milicevic, Simpson impressed from the outset and even warmed the bench in a UEFA cup tie against French side Marseille.
?Along with my debut, being involved in a game of that stature was unbelievable,? he recalled.
?I was really happy with how I was playing but unfortunately for me once again a new coach came in and I was on the outer.
?When the opportunity arose to sign a short term contract with Perth Glory in 2007 I jumped at the chance.?
Following some impressive performances in the purple jersey, the 23-year-old found himself on the cusp of Olympic selection, playing a few lead-up games ahead of the ill fated Beijing campaign.
He decided to spend last winter in the Telechoice Premier League with the Blacktown City Demons before his passport was stamped once again after FF Jaro, a club team in Finland, secured his signature.
?But once again a new coach came in at the worst possible time,? he said.
?I had scored three goals in ten games and was happy. But I wasn?t going to wait around for things to happen so I came home again.?
The chance to work under one of his former mentors in Aytec Genc at Sydney Olympic was too good to refuse, with Simpson agreeing to terms with the Greek club in February.
?I really enjoyed working with him (Genc) in my younger days at St George and it was disappointing to see him go,? he said.
?But when Nick Theodorakopoulos took over a few weeks ago I wasn?t going anywhere.
?I feel I have gone full circle after he (Theodorakopoulos) coached me at Parramatta and I am sure once we tighten up a few things we (Olympic) will be hard to beat.?
As for the future, Simpson hasn?t ruled out a third sojourn on foreign soil.
?You never say never but at the moment I am pretty settled,? he said.
?Football has been very good to me, taken me places I never thought possible.
?As long as I keep enjoying it I will be happy, I don?t worry about things I can?t control.?
-By Andrew Prentice