This research is designed to determine the relationship between English teachers' effectiveness and students' English proficiency at Selected Colleges in Dili, East Timor, as input for enhancement programs. The English teachers' effectiveness consist of three aspects namely (1) English Proficiency, (2) Pedagogical Knowledge, and (3) Socio-Affective Skills. Meanwhile, the students' English proficiency was measured in terms of the following aspects: (1) Listening, (2) Writing, (3) Reading, and (4) Speaking. The collected data is analyzed by using the Statistical Package for Social Sciences whereby charts, figures and tables were used to present the findings. The overall mean for English Teachers' Effectiveness is 3.64, interpreted as effective. This implies that English Teachers at Selected Colleges demonstrate the effectiveness required of them, but it is in Socio-Affective Skills that they are performing best. The overall mean for Student Respondents' Level of English Proficiency is 3.85, interpreted as good. Observing closely, the mean score of speaking which is 3.51 is close to "Average" (down) because in the Range of Mean Values of 2.51-3.50 is Average. The results of the Pearson Correlation showed that all independent variables on English teachers' effectiveness are correlated with the dependent variable on students' English proficiency. The correlation coefficient values are between of ± 0.50 to ± 0.74, which means "High or Strong Relationship". Based on a reasonable output of this study, the researcher proposed training programs to enhance the English teachers' effectiveness and students' English proficiency in Selected Colleges in Dili, East Timor.