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The history of pineapple cake is an educated guess for most food historians. Culinary evidence (cookbooks & magazines published in the United States) confirms pineapple was a readily available and very popular ingredient in the 1920s. This also happens to coincide with the popularity of the maraschino cherry. Details here:

"Pineapple cake
Food historians agree that pineapple cake belongs to the twentieth century but are not so certain about the decade. According to John Mariani's (The Dictionary of American Food and Drink, Revised Edition, 1994), "The first mention in print of such a cake was in 1930, and was so listed in the 1936 Sears Roebuck catalog, but the cake is somewhat older." In Fashionable Food: Seven Decades of Food Fads (1995), Sylvia Lovegren traces pineapple cake to a 1924 Seattle fund-raising cookbook...While rooting around in old women's magazines I found a Gold Medal Flour ad with a full-page, four-color picture of Pineapple Cake--a round cake with six slices of pineapple, candied red cherries, and a brown sugar glaze. The date: November 1925."
---American Century Cookbook: The Most Popular Recipes of the 20th Century, Jean Anderson (p. 432)