The midfielder joined Arsenal aged 15 back in 2008, but never made an appearance for the club.
Tottenham Hotspur completed an excellent piece of business when they agreed a deal to sign Dele Alli in the winter. According to the BBC the club agreed to pay £5 million for the midfield dynamo, sending him back to Milton Keynes on loan for the rest of the season as part of the deal.
This week a sign of his excellent form for the season emerged in the form of his nomination for the Sky Bet League One Player of the Year award.
He is of course a former talent at Tottenham's fiercest rivals Arsenal.
Arsenal snapped up Freeman from Gillingham in a deal reported by the BBC to be in the region of £200,000 in January 2008. He had previously become the club's youngest ever player at 15 years 233 days.
But the youngster, who Arsene Wenger once told Arsenal.com was an 'interesting prospect', failed to live up to expectations at The Emirates.
After five years and no appearances he moved to Stevenage, after a successful loan spell, and in the summer joined Bristol City.
This season he has been magnificent for The Robins, playing over 50 games and becoming their marquee player without a shadow of a doubt.
So while Alli is looking forward to a career in North London, Freeman has his in the past - and will now be hoping to lead Bristol City to the big time next season.