Research from sport has shown that reasons for drop-out can be related to aspects such as perceptions of low sport-specific competence, lack of enjoyment as well as team spirit, other things to do or an injury (e.g., Temple & Crane 2016). The primary objective of this study is to analyse the underlying factors that influence and interrelate drop-out behavior among young promising football players and compare how these factors can be understood in relation to age and gender. The study builds on 363 women’s and 170 men’s answer to an open question: Can you describe in your own words why you stopped playing club football? An iterative analysis was used to identify the constraints that influenced the players' decision to stop playing football. The findings show that a single reason for drop-out seldom exists. Different reasons are interrelated and it is a complex process. Overall are structural factors (e.g., injury) followed by interpersonal (e.g., other sports) and intrapersonal factors (e.g., lack of enjoyment) the most common noted underlying reasons for dropping out. Comparisons between age and gender demonstrate that drop-out trajectories are different for women and men at younger age (15-19 years) but that they become more similar in young adulthood (20-23 years). In conclusion, the study contributes with new insights into women’s and men’s dropout reasons and drop-out trajectories over time. One implication of the study is that youth football for girls and boys needs to find their unique solutions to ensure that more players play longer.