[5][6][7] Chipperfield began his professional career at Wollongong Wolves in 1996 and was a vital member of the team that won the National Soccer League twice in a row, in 2000 and 2001, and the Oceania Club Championship in 2001.

He twice won the Johnny Warren Medal for the most outstanding player in the Australian domestic season and gained interest from European clubs.

In early June 2001, Perth Glory announced that Chipperfield would be joining them for the 2001–02 NSL season, however he signed for FC Basel before his Wollongong Wolves contract expired at the end of the month.

The following season, he was an important member of the team as Basel reached the Second Group Stage of the 2002–03 UEFA Champions League, notching up wins against MŠK Žilina, Celtic, Spartak Moscow, Deportivo de La Coruña and Juventus on the way.

In the summer of 2006, Chipperfield was subject to an unsuccessful bid by Charlton Athletic to obtain his services, but Basel soon announced that he had signed a three-year contract extension.

As Basel qualified for the UEFA Champions League, after a six-year absence, in 2008, Chipperfield was one of only three survivors of the squad that competed in the competition in 2003, the other two being Ivan Ergić and Benjamin Huggel.

[15] At the end of their 2011–12 season Chipperfield retired from his professional career and moved to local amateur club FC Aesch as player-coach.

[16] On 1 June 2012 it was announced he had signed a short-term contract to play for Illawarra Premier League club Tarrawanna Blueys FC.

Chipperfield was part of the team that defeated Uruguay in a playoff in November 2005 to qualify for the 2006 FIFA World Cup in Germany, and was named in Australia's final 23-man squad.

[20] After the final group game of the 2010 FIFA World Cup against Serbia, which Australia won 2–1, Chipperfield announced his retirement from international football.