In 2002, Woolf began his coaching career as an assistant coach for the Townsville Brothers in the Townsville & District Rugby League (TDRL) competition. At the same time, Woolf was teaching at
Ignatius Park College and coaching their senior rugby league side, winning the Queensland State Schoolboys Championship in 2004. In 2005, Woolf joined the
North Queensland Cowboys as their junior development manager. After holding the role for four seasons, Woolf became the team's
NYC coach in 2009. He took the side to the finals for the first time in 2010 and to their first Grand Final in 2011, which they lost in
golden point to the
New Zealand Warriors. In 2012, Woolf joined the
Brisbane Broncos as an assistant coach to
Anthony Griffin. In 2015, he returned to North Queensland as the inaugural coach of the new
Intrust Super Cup side, the
Townsville Blackhawks. In the club's first season, the side finished in first place and qualified for the Grand Final, losing to the
Ipswich Jets. Woolf was appointed head coach of the
Tongan national team in 2014. In October 2015, Woolf recorded his first win with Tonga in the
Asia-Pacific 2017 World Cup qualifying game against the
Cook Islands. In 2016, Woolf's Tonga team suffered a second straight defeat by Samoa in the
2016 Polynesian Cup. In the
2017 Rugby League World Cup, Woolf guided Tonga to beat NZ Kiwi and a thriller with England at Semi Final. On 26 September 2018, Woolf officially left his role as Blackhawks' head coach, which he held for four seasons, to take up an assistant coaching position with the
Newcastle Knights. On 27 August 2019, Woolf was named interim head coach with Newcastle for the remainder of the 2019 season after
Nathan Brown stepped down. On 10 September 2019, it was announced that Woolf would take up the head coach role at
St Helens in 2020, signing a two-year contract with the club having the option to extend a further year. After defeating NZ Kiwi in 2017, Woolf led Tonga in 2019 to defeat both the British Lions Rugby League and the World Champion Australian Kangaroos. He coached St Helens in the club's 8–4
2020 Super League Grand Final victory over Wigan at the
Kingston Communications Stadium in Hull. He coached St Helens to victory in the
2021 Challenge Cup Final with a 26–12 victory over
Castleford at
Wembley Stadium. On 9 October 2021, Woolf coached St Helens to their
2021 Super League Grand Final victory over the
Catalans Dragons. On 24 September 2022, Woolf coached St Helens in their
2022 Super League Grand Final victory over
Leeds in his final game in charge of the club.
Tonga record Dolphins in 2026 In late 2022, Woolf was signed as an assistant coach by the
Dolphins for their inaugural 2023 season in the
National Rugby League competition. He became head coach for the 2025 season onwards when his mentor
Wayne Bennett moved on. In his first season as head coach of the Dolphins, Woolf guided the club to a 9th placed finish on the table just two points outside of the finals positions. The club were on course to make the finals but then they suffered an end of season slump losing three of their last five matches to finish just behind the
Sydney Roosters. ==Personal life==