Entrepreneurship education at Vocational High Schools (SMK) has a strategic role in equipping students with entrepreneurial competencies, skills and attitudes to face the challenges of the world of work and encourage the creation of independent and productive graduates. Therefore, an evaluation of the implementation of the entrepreneurship program needs to be carried out to identify the effectiveness of the program and aspects that require development. This study aims to evaluate the implementation of the entrepreneurship program at SMK YPI Darussalam 2 Cerme and SMK Muhammadiyah 3 Gresik using the CIPP (Context, Input, Process, Product) evaluation model through a qualitative approach with a multi-site study design. Data was collected through interviews, observation and documentation involving 12 informants, consisting of 2 principals, 2 deputy principals for curriculum, 2 deputy principals for student affairs, 2 deputy principals for community relations, 2 teachers and 2 students. Data analysis was carried out through per-site analysis and continued with cross-site analysis. The results of the study indicate that in the context aspect, both schools have a fairly strong foundation in developing entrepreneurship programs; in the input aspect, available resources are relatively adequate although there are still limitations in infrastructure and business capital support; in the process aspect, the program implementation has been running through theoretical and practical learning, but has not been fully optimal in mentoring and sustainability of student businesses; while in the product aspect, the program has a positive impact on improving student entrepreneurial competencies and attitudes although the resulting business results still vary. This study concludes that the CIPP model is effective for evaluating entrepreneurship programs comprehensively and can be a basis for consideration in developing entrepreneurship programs in schools.