Formal English language education in Taiwan now starts at Year 3 in primary school, with an emphasis on communicative proficiency. In addition to formal education, attending English cram schools after regular school has become a common phenomenon for Taiwanese students. The main purpose of gaining additional reinforcement in English cram schools is to help pupils enhance their academic performance. However, how pupils use strategies to approach their learning, how they prefer to develop their listening skills, and their relation to different learning environments, say, formal and cram schools, are still unclear. The aim of the present study is to investigate how far formal and cram school English education and the degree of English listening comprehension influences different aspects of listening strategy use and learning styles. The research involved a questionnaire survey of 526 Year 6 primary school pupils. The analysis of the questionnaire was conducted through multivariate analysis of variance and chi-square tests of independence. Results showed that there was a close link between English listening comprehension, learning in English cram schools, certain types of strategy use, and learning styles. Pupils who preferred to learn English in cram schools reported better English listening comprehension and developed better cognitive strategies.