He spent eight years within the Arsenal youth academy, and much like many current and past prospects such as Benik Afobe and Chuba Akpom, first team opportunities were few and far between.
Simpson was considered something of a star at Arsenal Football Club, but unfortunately for him, his impressive displays for the Arsenal reserves and his historic first ever hat-trick scored at The Emirates during the FA Youth Cup match against Cardiff City, would be the peak of his successes at the North-London club.
Much like many youth team players in the Premier League, Simpson seeked first team football, something he was failing to recieve at Arsenal. He was sent out on a string of loan deals with the opportunity to establish himself as one for the future and a saving grace for an Arsenal side who at the time, were lacking inspiration.
Simpson's first loan deal was with then League One side Millwall, he would impress for The Lions and later that season went on to win the PFA fans' player of the year award for 2008.
"Going to Millwall was the best decision I have ever made.
- Jay Simpson
The Englishman relished his opportunities with Millwall and was quick to thank the club for helping him develop his overall game which what he hoped at the time, would help him drive towards first team opportunities at his parent club, Arsenal.
"Playing regularly in the first team really developed my game. It helped me grow as a player and I made a lot of good friends. It did me the world of good. The Millwall fans were really good to me – and I appreciated their support."
His time out on loan didn't go unnoticed by the Arsenal hierachy, with club boss Arsene Wenger being quoted as stating (back in 2008) "It is too early to say if he [Jay Simpson] has a future, but I think so yes. He has done extremely well and has scored goals"
Having seen in an impressive New Year whilst at Millwall, Simpson waited until November for his Arsenal debut in the 6-0 win over Sheffield United in the League Cup, where he came on as a substitute in the 71st minute.
Despite not scoring upon his debut for The Gunners, Simpson would later go on the score his first and only goals with a brace in the 3-0 home win over Wigan Athletic, again in the League Cup competition.
Simpson would go on to make just three total appearances for Arsene Wenger's side, with all three of them coming from the League Cup competition. Despite some solid performances from the young Englishman, he struggled to compete with Arsenal's then-first team options; Eduardo da Silva, Nicklas Bendtner, Robin van Persie and Emmanuel Adebayor to name a few.
The inevitable outcome was to be another loan deal away from the club, giving Simpson another chance to prove to Arsene Wenger he is worthy of a place within the first team setup.
Despite being rewarded with a new contract at Arsenal, Simpson would sign for West Bromwich Albion on loan for the season, where he would score just once in thirteen Premier League apperances.
It was safe to say Simpson wasn't quite ready for Premier League football, having impressed in the lower leagues with Millwall, Simpson had proven himself at League One level and a third loan spell at a successive different club would present the pacy striker with a final opportunity to sway Arsene Wenger's mind.
Queen's Park Rangers signed Simpson on a season-long loan in August 2009, the striker would go on to make 39 league starts in the Championship and scored 12 goals in the process; a good return for any loanee.
However despite his best efforts, they would prove to be his last when Arsene Wenger allowed his former youth team prodigy to leave for Championship side Hull City for a fee of £1 million. He spent three seasons at The Tigers but failed to live up to his lofty price-tag and only managed to net 12 times in over 70 league appearances.
Following a dissapointing spell at Hull City where Simpson, despite showing moments of brilliance, failed to regularly find the back of the net for the Championship side, Simpson returned to Millwall for a second loan spell in the hope of rekindling previous form which saw him become a fan favorite with The Lions.
He played on loan for a little over five months but, much like his previous forays at various football clubs across England, Simpson failed to impress and live up to his full potential.
Much like many failed Arsenal youth team prospects, Simpson had to look for football outside of England. After over a year out of the game, he signed a two-year contract for Thailand's Buriram United which reportedly earned him £40,000 a month - reportedly making him the all time highest paid footballer in Thai history.
However just one goal in fifteen appearances, despite it winning the club the Kor Royal Cup, was not deemed good enough and the Englishman agreed to a mutual termination of his contract.
At present; Jay Simpson plays for League One side Leyton Orient, having signed on a free transfer in July 2014.
The former under-18 international adapted well in the early stages of life back in England and - having scored six goals from nine games - the striker is now looking to revive his career at a club who are also trying to revive their own fortunes. Having narrowly missed out on promotion via the play-offs in the 2013/14 season, Orient now find themselves in a relegation fight.