The twenty year-old midfielder hails from Horndean, originally but signed for The Saints of St Mary’s as a youngster before his talents were spotted and transferred North East, to Newcastle United in 2015.
At St James’ Park he progressed to their Under-21’s/23’s, where he matured further under the watchful eye of Tyneside legend, Peter Beardsley.
While in their Under-18’s, he played in the side that reached the quarter-finals of The FA Youth Cup; only bowing out to eventual winners, Chelsea and a line-up that featured future England Internationals, Tammy Abraham and Dominic Solanke.
He came even closer to glory when he moved up to the next level; as the Under-23’s narrowly lost out to West Ham United in the final of The Premier League 2 Division Two Play-Offs.
That stellar run of form was rewarded with a new contract, alongside eight of his fellow scholars.
Sadly, for Olly, however, he didn’t quite make that next – and biggest – step into the senior team and got released a year later, after three terms at the club.
Undeterred and despite his earlier connections to the red and white stripes on The South Coast, he impressed Pompey Boss, Kenny Jacket on trial, during the latter weeks of 2018-19.
Although, ultimately, no permanent move would come of his brief spell at the League One Blues, he was definitely considered as one to watch by the coaching staff at Fratton Park.