One of the most critical areas where considerable attention is required in teaching a foreign language involves listening skills. Listening plays an essential role in both communication and learning, and it is one of the most crucial necessary language skills in the field of language learning. Recent studies in foreign language listening have extensively focused on the prevailing difficulties of listening. There has been little research on the cultural-background as a sociolinguistic dimension of listening. Therefore, this study set out to determine whether Saudi EFL students face particular difficulty in their listening comprehension, to identify possible reasons for the problems, and to find out whether the cultural-background affects the listening process. To achieve these objectives, a triangulation method was followed. A diagnostic test and a questionnaire were used on a group of 31 Saudi students of English and a reflective essay was carried out on eight EFL teachers. The findings suggest, first, that listening is the most challenging language skill and, second, that Saudi EFL students encounter substantial difficulty in the perception, parsing, and utilization phases of their listening comprehension for many reasons. The findings also suggest that the cultural background has a significant effect on their listening process. This study is expected to contribute markedly towards increasing the understanding of listening difficulties in language learning, and improving the teaching-learning process, by recommending effective remedies for addressing such challenges.