Shillingford graduated from Teikyo-Westmar University with a Bachelor of Arts. She began working as a teacher in 1979, and eventually became principal of St. Andrews High School. She remained in education until she entered electoral politics.
She ran unsuccessfully for the Wesley seat in the House of Assembly in the 2005 general election. She was subsequently appointed as a Senator that year. Shillingford again contested the Wesley constituency in the 2009 general election. She won the seat on 18 December 2009, with 809 votes against 734 received by Ezekiel Bazil of the UWP (52.4% to 47.6%).
- 2009 candidate profile of Gloria Shillingford, Dominica Labour Party, retrieved 22 February 2011.
- Electoral Office (21 December 2009), House of Assembly General Election 2009 - Final Count, Commonwealth of Dominica, retrieved 22 February 2011.
- Address by Hon. Gloria Shillingford on the Occasion of the 19th anniversary of The Convention on the Rights of the Child (CRC), Commonwealth of Dominica, 10 March 2010, retrieved 22 February 2011.
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