Olly started playing with local clubs in Nottinghamshire and won several caps for his County FA. In 2006 he earned a soccer scholarship to William Woods University in Missouri. After four seasons in the NAIA and PDL with St. Louis Lions, Olly signed his first professional contract with the Missouri Comets in the Major Indoor Soccer League. After moving home and playing futsal for Loughborough University, Olly returned to the States with the Louisville Lightning. After an injury, Olly focussed solely on coaching; first with the Kentucky Fire Juniors and then with Advanced Total Soccer and Princeton Soccer Association in New Jersey. Olly again returned to professional soccer with the Seattle Impact, Ontario Fury and Jaco Rays. Olly has coached in England and several states across the USA – he is currently working towards his UEFA B coaching licence and continues to play semi-professionally.