The successes of web design by learning relates to the pre-service teachers' personality. Unfortunately, the relationship between personality and pre-service teachers' technological pedagogical content knowledge related Web (TPACK-Web) still uncertain. The main objective of this study was to explore the relationship between the Five-Factor Model (FFM) of personality and TPACK-Web of the pre-service teacher in Indonesia (N=309). To examine the correlation among two packages of variables, descriptive statistic, bivariate correlation, and Partial Least Squares-Structural Equation Modelling (PLS-SEM) was applied. The finding presented that the correlation between FFM of personality and TPACK-Web was significant. The most important finding suggested that Agreeableness, Conscientiousness, and Openness had a direct effect on the core of TPACK-Web bases (WK, PK, CK), and WPK to WPACK had the strongest effect. Finally, the implication of this study is provided along with suggestions.