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File consists of printed material and ephemera, such as invitations, pamphlets, programmes and related material regarding a number of Winsom's exhibitions, art auctions, and other artistic projects in the 1990s. Includes records relating to Uhuru Sasa/ Freedom Now (1991), Roundup (1992), Women Beyond Borders (1998), Winsom: In The Spirit (1999), and others. Also includes an artist statement and statement of thanks relating to an unspecified display.

File consists of records relating to Winsom's exhibitions and other projects with the Women's Art Resource Centre (WARC). Includes newsletters, brochure for Crossing Borders Mapping Boundaries, a WARC/WCA International Conference, media releases and invitations, and other printed material. Records relate to Making Peace With Ourselves: Art Against War (2000), For My Mother: A Visual Prayer/Feast (2003), and other projects.

File consists of records relating to the River of Life (2000) exhibition at the Thames Art Gallery, as well as other subsequent installations of River of Life. Includes promotional material, notes regarding opening and closing remarks, and related documents.

File consists of records relating to Winsom's solo exhibition, I Rise (2019), held at the Art Gallery of Ontario. Includes installation documents, crate lists, budget documents, and related exhibition documents.

File consists of audio-visual material relating to Winsom's exhibitions and projects. Optical disks contain a digital catalogue for Rousings (2004) featuring Winsom's artist statement, video footage from the opening of Iconography of Divination (2003) at the A Space Gallery, and "OYA + Yemaya," a movie by Winsom. Also includes the movie All Eyes on Africa (1993) by Clem Marchall on VHS and a VHS tape titled "Interview Grand Cayman - Looking for perfect teachers 2004."

File consists of records relating to the Winsom Foundation, a Belize-based non-profit organization established by Winsom in 2007.includes printed material such as a brochure, flyers, and event posters, an Art Journal by the Art Students of Cristo Rey R.C. School (a project that was supported by the Winsom Foundation), as well as correspondence, a certificate, and a form relating to a tour of the National Institute of Culture and History (NICH). Also includes a copy of the publication This is How We Keep Breathing: Voices from Belize & Beyond..., which is an anthology of poetry and short stories resulting from a collaboration between OCAD U and the Winsom Foundation. Winsom also contributed writings and illustrations to the publication.

File consists of an event menu, invitations, newsletters, and other material featuring art and illustrations by Winsom. Includes the Kingston Jamaica YMCA Camp Councillor's Training Manual featuring Winsom's illustrations and the premier issue of the Jamaica Pat Boone Magazine, which includes a short story by Winsom on page 13, as well as a note across pages 14-15 reading "my page."

File consists of 16 pages of sketches and illustrations by Winsom, as well as one dyed textile work of Winsom's name glued to paper. Includes pattern designs, cards, motifs for fabric, and other sketches. Materials are predominantly undated.

File consists of Winsom's business cards, member cards, badges, and name cards for events and speaking engagements. Includes three business cards, a CARFAC member card and five name cards relating to events and talks, such as the Dagara Shamanic African Diaspora Training (2003-2004) and the Belize International Film Festival (2005).

File consists of an autograph notebook containing notes and letters written to Winsom throughout the 1960s.