This study investigates the teacher’s strategies in teaching contextual English. This study is a qualitative study. This study is also cased study. As many as three English teachers from SMK N 1 Wadaslintang, Wonosobo, Indonesia, participated in the study. They were recruited on a convenience sampling basis. Observation, interview, open- ended questionnaires are used to collect the data. The findings have shown that the strategy used by three English teachers of SMKN 1 Wadaslintang in implementing teaching contextual English varied from Discovery learning, Project Based Learning, CTL by applying REACT strategy, and contextual English or ESP. The implementation of strategy in implementing contextual English can engage the student’s participation in the classroom. The behavioral facet, the strategies show that the students were active in the learning process. In the cognitive engagement, the strategies show that the students focus their attention on completing the task or meeting learning objective and in social engagement dimension, the strategies show that the students get involved in teamwork, having communicative skill in the interaction among the students and the teacher