This study purposed to investigate the influence of the head teachers’ leadership styles on pupils’ academic performance in Trans Nzoia West Sub County. The specific objectives of the study were to find out the influence of autocratic leadership style, to investigate the influence of democratic leadership style, to establish the influence of laisses faire leadership style and to determine the influence of charismatic leadership style of head teachers on pupils’ academic performance in Trans Nzoia West Sub County, Kenya. The study was pinned on Leadership Theories by Fielders’ Work. Descriptive survey research design was employed. A sample size of 302 respondents was determined from a target population of 1366 people using Krejcie and Morgan Table. Questionnaires were used in collecting primary data. The instrument was tested for reliability using Cronbach’s Alpha Reliability test while content validity was assessed using expert opinion. The study employed both descriptive and inferential statistics in analysis and used correlation and regression analysis as key analytical models. Results established varied disparities in pupils’ academic performance. Regression results demonstrated that head teachers’ leadership styles (autocratic, democratic, laisses faire and charismatic leadership style) all yield statistically significant influence on pupils’ academic performance. The Coefficient of Determination or R square stood at 0.763, which implied that 76.30% of the variation in the pupils’ academic performance was explained by variability in the variables under head teachers’ leadership styles (autocratic, democratic, laisses faire and charismatic leadership style). Pearson Correlation Analysis results further demonstrated a positive relationship between all head teachers’ leadership styles assessed; autocratic, democratic, laisses faire and charismatic leadership style on pupils’ academic performance. The study recommends more pursuit of head teachers’ leadership styles as demonstrated in the Fielders’ Work framework to enhance pupils’ academic performance. Investors, school management, government, researchers and academicians will greatly benefit from this study as it provides viable insights that could guide decisions to serve their interests on the critical subject of enhanced pupils’ academic performance.