[6] In 1985, he represented NUSAS UCT in the Education Charter Campaign led by the non-racial student movement.

[10] In 1991, he became a member of the African National Congress and was involved in the Rondebosch (Gaby Shapiro) branch.

He was elected to the African National Congress Regional Executive Committee and was soon appointed the head of the organising department in 1992 and 1993.

He was also appointed the head of the African National Congress Western Cape Elections Voter Organisation and Training (VOT).

[12] In 2004, Premier Ebrahim Rasool appointed Dugmore to the post of Provincial Minister of Education.

[13][14] Dugmore left the Provincial Parliament in 2009 and was consequently appointed as convenor of the ANC Overberg Fishing Task Team.

[18] In 2018, Dugmore declared his candidacy to replace embattled former ANC Western Cape Chairperson, Marius Fransman.

On 20 May 2019, the African National Congress named him the incoming Leader of the Opposition in the Western Cape Provincial Parliament.

[20][21] Dugmore was criticized for attending a Russian consulate event on 28 February 2022, four days after the start of Russia's 2022 invasion of Ukraine.

[22] Dugmore's position was criticised by the Financial Mail as a type of "moral relativism" that ignores an "unprovoked, illegal invasion of a sovereign state.

[24] He lost to the party's former Dullah Omar regional secretary, Vuyiso JJ Tyhalisisu, who was nominated from the conference floor, by 29 votes.

[25] Dugmore then successfully stood for election to the Provincial Executive Committee as an additional member.