Though revising the existing syllabus is part of the Ethiopian education system, the study of the implementations of the notions of the syllabus attracts a few researchers' interests. Therefore, this study investigates teachers' practices of teaching speaking and compares them with the principles of Communicative Language Teaching (CLT), the underlying approach of the new syllabus. It also explores teachers' rationalizations of their practices and the factors that influence the teaching of speaking. To achieve the objectives, the researchers used a qualitative case study research design. The data from the four purposively selected English teachers was gathered through classroom observations and stimulated recall interviews. In analyzing the data, a qualitative content analysis method was used. The results of the study showed that 1) the major activities and teaching cycle the teachers employed were similar, 2) most of the actual classroom practices did not match with the principles of Communicative Language Teaching, and 3) there were learner-related, teaching-related, curricular, and environmental factors that influenced the teachers' enactment of the principles of CLT and the teaching of speaking in general. The predominant influencing factors were the learner-related: Lack of basic background skills, lack of experience in practicing speaking lessons, the use of mother tongue in pair and group work activities, fear of making mistakes, lack of interest in speaking lessons, and excessive focus on standardized tests.