The Ivory Winston papers date from 1936 to 2010 and contains of three newspaper articles concerning Winston's career, two programs and a print advertisement, two photographs (one candid of Winston holding a bouquet, the other of a posed Winston and other women in formal wear, and an article on the Winston family history in Ottumwa. An oversized poster housed in the map case features a photo of Winston, with a caption from the Ottumwa Daily Courier describing how "Senator Alben Barkley of Paducah, Kentucky, candidate for vice president, brushed a nostalgic tear from his eye as he shook hands with Mrs. Clyde Winston for her singing of 'My Old Kentucky Home'."