Traditionally, golf instruction has been oriented toward imitation of role models, guided by errors that surround a channel of supposedly correct repetition. Recent motor learning approaches relying on the dynamics of living systems suggest the inclusion of additional noise during practice for supporting players’ movement exploration and improving adaptability that in consequence will lead to increased performance. While the effectiveness of this approach has now been demonstrated in many sports, research exploring the effects of differential learning (DL) in golf is scarce, especially when considering different shot distances and players with various handicap levels. Therefore, the purpose of this study was to compare the effects of an enriched learning and information intervention as opposed to a more constrained approach, on the pitching performance of golfers with different handicaps from different distances. A total of 29 adolescent golfers with an average experience of 7.8 years were divided into a DL (n = 15) and a repetitive-oriented (RB, n = 14) group. Both groups were further compared dependent on their handicap level (DL, low handicap n = 7, high handicap n = 8; RB, low handicap n = 5, high handicap n = 9). The TrackMan 4 was used to measure the shot performance for 20 m, 35 m, and 50 m distances (10 shots from each distance) based on a pre- and post-test design. Each group performed the same number of trials (n = 270, 9 executions per distance per session) across 10 sessions. Analysis of covariance (ANCOVA) was used for the statistical analysis, using the pre-test as covariate and the post-test as dependent variable. The DL group revealed advantageous adaptations in the attack and face angle (p ≤ 0.05), while also in the dynamic loft (p ≤ 0.05), mostly for the 35 m and 50 m. In addition, this intervention led to improvements in the score, club head speed, and carry distance for the 50 m when compared to the RB (p ≤ 0.05; small effects). The low handicap players from the DL group also revealed adaptation in the angles’ variables (p ≤ 0.05) when compared with high handicap players, who improved the score (p ≤ 0.05) in all distances after intervention. The low handicap players from the RB group improved the score (p ≤ 0.05) and club speed (p ≤ 0.05) for the 20 and 35 m, while the high handicap golfers revealed higher improvements for these variables only in the 50 m distance condition. Overall, coaches may incorporate approaches into their skill training that increase the number of opportunities to improve the performance of both experienced and non-experienced players by promoting the adaptability of movement patterns.