Stephen started his footballing life as a teenager for his home town club, Marine FC. Aged 17, in 2015, he joined St Helens Town when first team football was unforthcoming at Marine. This proved a good moved for the left back, making 90 appearances for the club and scoring 16 goals over a two season period. In 2016/17 season, he was made first team captain, named plater of the year, young player of the year and under-21 player of the year. Such accolades drew the attention of Morecambe, and Stephen joined the Shrimps into their youth development program, also joining Clitheroe to play under gaffer Simon Haworth. Simon was so impressed, he was one of the players he has brought with him to Celtic.