The purpose of this study was to analysis of the challenges and problems of teachers’ assessment and evaluation. The main focus of this study was to investigate the extent of utilizing the assessment and evaluation and its implementation. Four high schools in Adigrat town were selected. Of the respective total population size of the study group, 4 principals, 60 teachers and 200 students as sample size were taken. The data for analysis were collected from students, teachers and school principals in each high school using structured interview and instrument. Prior to the data collection, a pilot study was made to see the reliability and face validity of the instrument for students and teachers, found to be 0.77 and 0.89 in Cronbach alpha respectively. After having the intended data, one sample t-test statistics was employed on the data. Both qualitative and quantitative data analysis has accomplished in identifying major and distinct challenges and problems including large class size, shortage of resources, inadequate knowledge of teachers, students’ poor educational background, inadequate supervision of school principals and other concerned bodies. The study came up with the conclusion of the applications of various assessment and evaluation methods in high schools were inadequate.