Parental involvement in youth sports is an increasingly relevant topic because of its key implications for children’s development in youth sports. This study’s aims are threefold: (1) to investigate parental involvement practices based on parents’ previous sports experiences, (2) to examine athletes’ and parents’ perceptions on parental involvement practices across different age categories, and (3) to compare the athletes’ and parents’ overall perceptions on parental involvement practices. In total, 423 participants (151 youth players and 272 parents) completed the Parental Behaviors in Sports (PBSP) questionnaire. The PBSP includes separate versions for parents and athletes, each assessing five key dimensions: (1) sports support, (2) competition attendance, (3) technical influence, (4) performance pressure, and (5) sports expectations. In the parents’ group, 154 participants (56.6%) reported previous sports experience. No statistically significant differences were observed in the PBSP dimensions between parents with and without previous sports experience. Parents’ years of sports experience negatively correlated with performance pressure (r = −0.155, p = 0.013) and expectations (r = −0.149, p = 0.017). Age group analysis showed lower competition attendance in the U18 group and higher expectations in the U12 group. When comparing parents’ and athletes’ responses, statistically significant differences emerged in all PBSP dimensions except for performance pressure. These findings underscore the importance of aligning parental involvement with children’s experiences to foster enjoyment, reduce pressure, and support sustained engagement in youth sports.