Purpose The present study investigates to what extend de-contextualized practice is necessary to acquire technical skills in developmental soccer training. Typically, open play is considered beneficial for acquiring tactical skills, whereas specific drills are used to support the development of technical skills like passing and shooting. Therefore, a field-based study was designed to investigate the effectiveness of a Nonlinear Pedagogy (NP) approach in contrast to a classical Deliberate Practice approach to improve passing performance in young developmental soccer players. Method Forty young male players (age 10 ± 1 years) were randomly assigned to three groups (PLAY, PRACTICE, and CONTROL). The PRACTICE group performed classical passing drills, whereas the PLAY group underwent a NP training regime. Passing skill was assessed before and after a 5-week training program using a standardized passing test according to the German Football Association. Additional retention testing was performed 5 weeks later. Results The results indicated that, although the test design showed no specificity to the learning environment of the PLAY group, both groups improved passing skills after training, but the PLAY group displayed better results during retention testing (PRACTICE: p = 0.004, d = 0.48; PLAY: p = 0.001, d = 0.53) compared to the PRACTICE group. These findings are suggestive of general transfer learning in dynamic learning environments. Conclusion The findings indicate that even when there is an emphasis on “technical skill” enhancement, more effective improvement in young development players may be observed through dynamic learning environments. Consequently, this study encourages coaches to design training regimes that afford players to train as they play.