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.

[10] In the 2017 Rugby League World Cup, Woolf guided Tonga to beat NZ Kiwi and a thriller with England at Semi Final.

[11] On 27 August 2019, Woolf was named interim head coach with Newcastle for the remainder of the 2019 season after Nathan Brown stepped down.

[12] 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.

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.

[17] In late 2022, Woolf was signed as an assistant coach by the Dolphins for their inaugural 2023 season in the National Rugby League competition.