Ollie started dancing with the Dorothy Coleborn School of Dancing when he was 5 years old. He studied Ballet, Tap and Modern and when he was nine he became Junior Associate of the Royal Ballet School, and later a Mid Associate. Ollie performed with The Northern Ballet in Dracula, Madame Butterfly and Christmas Carol. He also played the part of "Chip" in Beauty and the Beast and performed in Jungle Fever and travelled with the dance school to perform as "Jeremy" in Chitty Chitty Bang Bang.
He first auditioned for the part of Billy Elliot when he was ten and then completed the transition to stage in the shortest time ever of just over a year. The training initially involved private coaching with Karen Paisey and Annette Hind and then eventually living in London and training on a daily basis.