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Cullen's provincial career started in 1994 season for Horowhenua-Kapiti. In 1996 he played in the first-ever Super 12 game, contested by the Hurricanes and the Blues. That year he scored seven tries in nine matches. At the 1996 World Sevens competition in Hong Kong he scored 18 tries, including seven in one match. Later that year he was selected as an All Black. He scored seven tries in his first two Test matches: a hat-trick on debut against Samoa and four tries against Scotland. He sustained a knee cartilage injury on the All Blacks' tour to South Africa. In 1997 Cullen returned from injury and scored 11 tries in 10 games for the Hurricanes, and 12 tries in 12 Test matches for the All Blacks. The All Blacks had a poor year in 1998 with five consecutive losses, but Cullen scored four tries in seven matches. He represented New Zealand in rugby sevens at the Kuala Lumpur Commonwealth Games, playing seven games, scoring nine tries and kicking 23 conversions. New Zealand won the tournament and the gold medal. In 1999 Cullen was a member of New Zealand's unsuccessful Rugby World Cup squad. He played six matches in the Cup tournament, starting five at centre which was not his preferred position. In 2000 he scored 10 tries in 11 games for the Hurricanes and seven tries in four Tri Nations Tests, including three consecutive pairs. In 2001 Cullen sustained a severe knee injury that required surgery and an intensive recovery programme. He made himself unavailable for the All Blacks' 2001 end-of-year tour, but was announced 'dropped' by coach John Mitchell at a NZRU press conference. Cullen and Mitchell's personal differences went unresolved over time. Cullen was selected to and dropped from the All Blacks squad throughout 2002. He scored four tries in the five Test matches that year. In the 2003 Super season Cullen scored eight tries in 12 games for the Hurricanes, taking his Super Rugby career tally to 56, a record at the time. He was briefly and controversially selected for the Māori rugby team, despite having, according to his father, about 1/64th Māori ancestry. He was left out of New Zealand's 2003 World Cup squad. He played out the NPC season for Wellington and received a standing ovation after the Championship final, despite Wellington's losing to Auckland. At the end of 2003 Cullen moved to Ireland, after he was dropped by John Mitchell, where he played for Munster. His time with Munster was blighted by injuries, particularly to his shoulder, limiting his appearances. His last match for Munster was a 15–7 Celtic League win over the Newport Gwent Dragons at Musgrave Park on 28 April 2007. Two weeks later, on 12 May, he announced his retirement from rugby and stated his intention of returning to New Zealand to start a business.
