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Cunliffe first played for Guam’s Tumon Soccer Club at the age of five. He was part of the Houston Texans team that won two youth national championships in 2001 and 2002, and was part of the 2001 Texans team that won the Brazil Cup. Cunliffe played for the NCAA Division I men’s soccer team, the Santa Clara University Broncos, including playing for its 2003 team that competed in the NCAA Final Four.

He made his first hat-trick for Guam in the 2013 EAFF East Asian Cup match against the Northern Mariana Islands, which helped them to win 3-1. He scored another hat trick against Bhutan in a 2022 World Cup qualifier on 11 June 2019, which ended 5-0 for Guam.

He made his 50th international cap on September 4, 2018 in Guam's match against Macau at the 2019 EAFF Football Championship. He is the first Guam national team player to achieve the said feat.

After his stint with the Philippine club, Cunliffe returned home to Guam to join Rovers FC. He played for the Rovers from 2013 to 2018, including the 2017 AFC Cup playoff qualifiers. He then moved to Bank of Guam Strykers FC and played for them at the 2018 Guam FA Cup.

From 2010 to 2012, he played for Guam Shipyard in the Guam Men's Soccer League. In 2012, he signed for Philippine side Pachanga in the United Football League.

He first represented Guam at youth level for its under-16 national team. He made his senior debut in the 2006 AFC Challenge Cup, with his first match as a starting player on 3 April 2006 against the host nation, Bangladesh. Since 2006, Cunliffe has become a mainstay in the national team and has been captain since 2012.

Jason Ryan Quitugua Cunliffe (born 23 October 1983) is a Guamanian footballer who plays as a midfielder for Bank of Guam Strykers in the Guam Soccer League, and is the current captain of Guam.