Bromley, Cardiff City, AFC Wimbledon, Episkopi, Kingstonian
Jessie started his playing career at Bromley Town in the U14's where he was spotted by Cardiff City scouts whilst playing later for the U16's
Having signed for Cardiff and subsequently failing to break into the First team he was then loaned out to AFC Wimbledon in February 2013. Jessie made his League Two debut for AFC Wimbledon two days after his loan commenced, appearing as a second half substitute for our very own Gary Alexander.
Jessie was released by AFC wimbledon at the end of the 2013 season after helping them secure their league status and he then returned to Cardiff who subsequently released him.
The 2013/14 season saw Jessie sign for Greek club Episkopi on a three year contract which he cancelled after four appearances due to personal reasons.
Returning to England Jessie then signed for Kingstonian last season from where he joined Greenwich for the start of this season 2014/15