The aim of this study was twofold: firstly, to identify the variables associated with the experience of penalty shooters, and secondly, to understand the interaction of contextual variables and penalty execution that differentiated experienced from inexperienced players. To achieve this, a systematic observational methodology was employed to analyze 1,589 penalty kicks in various international club and national team competitions for men. The analyses were conducted using contingency tables and the chi-square statistic, as well as decision trees and binary logistic regression, to address the second objective. Categorizing players as experienced or inexperienced was based on their role as penalty kick takers in the team. Considering experience, statistically significant differences were found in contextual variables such as the specific position, age, timing, and match status. Similarly, differences were found in the shooter's running approach and kick height. At a multivariate level, both classification models showed significant differences in shooting patterns based on experience: players differed in terms of match timing, the specific position, the running approach, and the penalty outcome. The results of this study demonstrated differences between experienced and inexperienced players, highlighting the need to: i) delve deeper into research on this specific soccer action, and ii) enhance training of such actions among a greater number of players, not solely relying on experienced players for their execution.