Olly started in the Bristol Rovers Academy and progressed through the youth ranks, before signing for Championship side Blackburn Rovers in August 2014 and linking up with their under-18s at the age of 16.
Olly returned to Bristol Rovers in August 2015 as a second-year scholar, becoming a part of the under-18s side at The Memorial Stadium.
In March 2016, he gained his first exposure to senior football on loan with Southern League Division One South & West side Mangotsfield United, scoring three goals and assisting one in four appearances.
In March 2016, he joined Southern League Division One South & West side Shortwood United on loan until the end of the season, scoring two goals and assisting three in 10 games.
Olly departed Bristol Rovers at the age of 18 in the summer of 2016 following the end of his scholarship, and was quickly snapped up by National League side Forest Green Rovers in June 2016.
He returned to Southern League Division One South & West side Mangotsfield United in August 2016, scoring one and assisting two in four games.
The forward then joined Southern League Division One South & West club Salisbury FC on a three-month loan in September 2016, scoring six goals and assisting four in six games while being an unused substitute four times.
He was recalled by Forest Green Rovers six weeks into his Salisbury loan and immediately loaned out to Southern League Division One South & West side Mangotsfield United on a month’s loan in October 2016, which was then extended for an additional month in November. During his third spell at the Mangoes, he scored four and assisted four in eight games.
In January 2017, he signed for Southern League Premier Division club Cirencester Town on a month’s loan, making three appearances and being an unused substitute once.
The striker moved on loan again in February 2017, this time to Southern League Premier Division club Dorchester Town for a month where he scored three goals and assisted one in seven games.
The striker then spent the rest of the season back with Forest Green Rovers, making his debut as a substitute in the National League away at York City on the final day of the 2016-2017 season.
The next season, Olly joined Southern League Division One South & West club Taunton Town in August 2017 on loan until the New Year. He made five appearances and scored one goal under Leigh Robinson before being recalled early by FGR in September.
In January 2018, he joined Southern League Division One South & West team Salisbury FC on a one-month loan for a second time, scoring four goals in six games.
He joined Southern League Division One South & West team Bideford on a one-month loan in February 2018, playing four games in North Devon.
In March 2018, he joined Southern League Division One South & West team Evesham United on loan until the end of the season. While at Evesham, he helped the club reach the league Playoffs where they lost out in the semi-finals to Swindon Supermarine. During his short spell in Worcestershire, he scored two goals in eight appearances.
Olly’s two-year spell with Forest Green came to an end when he departed the club in the summer of 2018, and spent part of the summer on trial with National League South side Bath City.
He opted to sign for Southern League Division One South side Yate Town in the summer of 2018 however, being part of the Bluebells squad that gained promotion from the league via the playoffs in 2019 which included two goals in the final against Cinderford Town. During his time at the club, he scored 23 goals and assisted three in 67 games, being an unused substitute twice.
In November 2019, he moved on to Southern League Division One South side Bristol Manor Farm, scoring one goal in 15 games under Lee Lashenko.
Olly returned to Southern League Premier South side Yate Town in the summer of 2020, leading the line effectively as Yate achieved their highest league ranking with a 7th-placed finish in 2021-2022 as well as helping them reach the FA Cup First Round in the same season and achieving silverware in the Gloucestershire Senior Cup. During his second spell at Yate, he made 72 appearances and was an unused substitute twice, scoring 22 goals and assisting 21.
In October 2022, he signed for Southern League Premier South side Tiverton Town on a permanent basis, making 13 appearances and assisting three goals during his three months at The Ian Moorcroft Stadium.