Career
Cahill began his career with Clonmel Town FC, one of Ireland's top junior football clubs winning an FAI Junior Cup winners medal with them in 1994. He then spent two seasons at Northampton before returning home in the summer of 1996. Despite playing a friendly for Waterford United against Southampton he signed for Cork City. After six seasons at Cork he moved to Shelbourne in the summer of 2002. While he was with Shelbourne he won the League of Ireland championship in 2003, 2004 and 2006. Cahill was signed by Drogheda United on 23 December 2006. With Drogheda, Cahill won his fourth Premier Division title in five seasons and a Setanta Sports Cup winners medal in 2007.
Cahill signed for Shamrock Rovers on 16 January 2009 along with Stephen Bradley in what was Michael O'Neill's first signings. He departed Shamrock Rovers in July 2010 after making 52 appearances for the club. and soon signed for Sporting Fingal.
When Sporting went out of business in February 2011, Ollie moved to Dalymount Park where he joined Bohemians, making his competitive debut against Portadown in the Setanta Sports Cup.
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