Clonmel born Ollie began his career at Northampton Town in 1994 and spent two seasons with the club before returning to Ireland in the summer of 1996 to sign with Cork City.

In six seasons at Turners Cross Ollie established himself as a quick winger with an eye for goal and became a firm favourite with the home crowd. However, in the summer of 2002 Ollie transferred to Shelbourne where he won three league titles in 2003, 2004 and 2006 and made over 150 league appearances.

By now converted to a wing back, Ollie was released at the end of the 2006 season as financial problems overcame the Dublin club and he signed with Drogheda United in 2007 where he won a fourth league title. After two seasons at United Park Ollie was on the move again, signing for Michael O'Neill at Shamrock Rovers in January 2009.

In July 2010, having made 45 league appearances for the Hoops, he moved across the city to join Liam Buckley's Sporting Fingal. Ollie made 13 league appearances for the 'Ravens' in the second half of 2010 and when the club folded in February 2011 Ollie signed for Pat Fenlon at Bohemians.

Ollie made 24 league appearances for Bohemians in what would be Fenlon's last season in charge at Dalymount Park and when his contract expired at the end of the year he hung up his boots and walked off into the League of Ireland sunset.