He was a 2007 AIS Football scholarship holder and was an influential player in their successful campaign in the Victorian Premier League.

Holland made an A-League debut with the Newcastle Jets playing two games as a short-term injury replacement player.

Holland was part of the Newcastle Jets team which won the 2008 A-League Grand Final against the Central Coast Mariners.

On 11 January 2009, Dutch club AZ Alkmaar completed the signing of the Australian midfielder for $650,000 (€350,000) on a four-and-a-half-year contract from the Newcastle Jets.

On 19 January 2011, it was announced that Holland would be playing for Eerste Divisie club Sparta Rotterdam for the rest of the season.

[11] On 18 January 2017, it was confirmed that Holland had joined Chinese Super League club Liaoning Whowin alongside fellow Australian Robbie Kruse on a two-year deal.

[13] James is an Australian Under-20 and Under-23 national team representative, a striker in this squad playing alongside Marko Jesic, Holland's good friend.