Ollie Dewsbury joined Bristol Rovers at seven years old and came off the bench to debut in the Gas' 7–2 victory over Whitby Town in the first round of the FA Cup on November 4 2023, becoming the second youngest player to represent the Pirates at senior level.

The forward remained around the squad and trained with the first team ahead of the 2024/25 season, playing again in Rovers' 3-3 draw against Tottenham Hotspur U21s in the EFL Trophy.

Dewsbury went out on loan for the first time in September 2024, joining Southern League Division One South club Yate Town. He made 14 appearances for the Bluebells and scored six goals.

The 17-year-old then had a temporary spell at Taunton Town, where he netted once in four outings.

Dewsbury was then recalled by the Gas and made his league debut as a late substitute against Huddersfield Town, where he was one of four academy graduates on the pitch.

The youngster has also represented Wales across multiple youth groups.