Born in Olinda, Pernambuco, Woolley played footvolley professionally before retiring and subsequently graduating in Physical education.
Woolley subsequently worked as a youth coach for Retrô and Náutico,[2] before becoming an assistant of Nilson at Flamengo de Arcoverde for the 2019 season.
[3] He led the club to the runner-up position in both the 2022 and 2023 editions of the Campeonato Pernambucano, but was sacked on 13 May 2023, after a winless start in the year's Série D.[4] On 22 June 2023, Woolley was named Campinense head coach, replacing sacked Luan Carlos,[5] but left on 25 July after just five matches.
[6] On 25 September, he was announced as the head coach of Manauara for the upcoming season,[7] but was dismissed the following 25 January, after just two matches.
[10] On 1 October 2024, Woolley agreed to return to Retrô as head coach for the ensuing campaign, with the club now in the Série C.[11] The following 12 January, however, he was sacked after two winless matches,[12] and took over Iguatu late in the month.