Literature-in-English is a major school subject that equips students with language and other soft skills needed for entry into the workforce. For students to acquire the skills, effective teaching, which is dependent on the availability of basic teaching–learning resources, is essential. Education is underfunded in Nigeria. This affects the quality of teaching and impedes learning. The rate at which students fail Literature-in-English, which is getting worse each year, indicates that there is a problem in the teaching–learning process. Using a mixed-method research design, this study investigated the problems of teaching Literature-in-English in 51 public senior secondary school in Ibadan metropolis, Oyo State. Random and purposive sampling techniques were used to select three local government areas (LGAs), 20 teachers, and 7,090 students. Data were gathered through Availability of Literature Teachers Checklist (ALTC), Interview Guide for Literature-in-English Teachers (IGLT) and Students’ Text Possession Checklist (STPC). The result shows that teachers are faced with a lot of challenges that prevents them from delivering quality instruction. These include poor learning environment, acute shortage of textbooks, low language proficiency misconceptions about the value of literature, heavy workload, and lack of parental support. Some schools do not have literature teachers. The biggest obstacle, however, is lack of textbooks. The situation is critical and points to a crisis of teaching and learning in Literature-in-English classrooms. Urgent interventions are needed if the objectives of this school subject are to be achieved. Some recommendations were made.