Background: This study contributes to expanding the existing literature on learning technical skills in youth soccer by comparing the effectiveness of different training approaches in the development of passing skills. The ecological-dynamic approach, which emphasizes the continuous and adaptive interaction between the athlete and the environment, is analyzed in comparison to the traditional prescriptive approach, which relies on predefined techniques and exercises. The aim of the study is to determine which of the two approaches is more effective in improving the performance of young soccer players. Methods: Thirty players (age 12 ± 1.2 years) were randomly assigned to two groups: the ecological-dynamic group (ECG) and a control group (CON). Both groups underwent an eight-week training program with equal sessions. The ECG group’s training focused on adjusting constraints like the learning environment, game rules, and visual restrictions to boost adaptability and problem-solving skills. The CON group followed a traditional prescriptive approach with specific instructions, goal setting, immediate feedback, and structured exercise progression. Passing abilities were evaluated before and after the program using the Loughborough Soccer Passing Test, with a retention test administered five weeks later. Descriptive statistics, including mean values and percentage improvements, were used. A repeated measures ANOVA compared differences between the groups. Results: The analysis revealed a significant Occasion × Group interaction for all performance variables, indicating that the ECG group experienced greater improvements than the CON group. Specifically, the ECG group showed significant reductions in Trial Time (p = 0.001, ηp2 = 0.6), Penalty Time (p = 0.016, ηp2 = 0.4), and Overall Performance (p = 0.011, ηp2 = 0.8) from pre-test to post-test. However, these improvements did not persist into the retention test (p = 0.131, p = 0.792, and p = 0.192, respectively). The CON group also improved significantly in Trial Time (p = 0.003), Penalty Time (p = 0.002), and Overall Performance (p = 0.001) from pre-test to post-test, but with smaller effect sizes and no sustained gains at retention. Conclusions: The ecological-dynamic approach (EDG) has proven to be more effective in enhancing passing skills compared to the traditional prescriptive approach (CON). Although both methods led to performance improvements, the EDG group achieved more significant progress.