The authors present an analysis of bilingual reading textbooks published at the turn of the 20th century. The authors examined the kinds of opportunities for learning offered by bilingual reading textbooks developed for students in Cuba, Puerto Rico, and the Philippines in the aftermath of the Spanish-American War. The analysis revealed challenges to understanding related to both the content and the structure of these textbooks, as well as the coloniality of knowledge embedded in them. The historical record also reveals a rejection of the format and content from scholars and educational leaders, and the subsequent turn toward reading materials, which better reflected the everyday experiences of Cuban, Puerto Rican, and Filipinx children, albeit often monolingually rather than bilingually. Implications are offered for how contemporary literacy materials might support (bi)literacy development of bilingual students across the globe.