Background: There is growing evidence indicating that physical education and sport (PES) are environments that, when appropriately structured, can promote positive youth developmental outcomes. In recent years, a number of researchers working in PES have designed programs and interventions aimed at helping teachers and coaches teach life skills and values. However, such efforts have lacked long-term assessments. Purpose: The present study consists of a two-year follow-up assessment of the Koh, Ong, and Camiré [2014. "Implementation of a Values Training Program in Physical Education and Sport: Perspectives from Teachers, Coaches, Students and Athletes." Physical Education and Sport Pedagogy. Advance online publication] values training program for teachers and coaches. The participating school's four values (i.e. integrity, resilience, commitment, and respect) were integrated within the training program. The study was guided by three research questions: (a) how have the teacher and coaches taught values since their involvement in the values training program? (b) for the teacher and coaches, what have been the challenges faced in teaching values through PES? and (c) how have the students and athletes applied, in and beyond PES, the values learned from the teacher and coaches who took part in the values training program? Participants: Three of the six participants who originally took part in the aforementioned study by Koh, Ong, and Camiré. [2014. "Implementation of a Values Training Program in Physical Education and Sport: Perspectives from Teachers, Coaches, Students and Athletes." Physical Education and Sport Pedagogy. Advance online publication] study were interviewed two years after having taken part in the values training program. The three participants (one teacher, two coaches) were all males between 34 and 35 years of age. Twelve of their current grade six students and athletes (10 males, 2 females), who were all 12 years of age, were also interviewed. Finally, three parents (one male, two females) of the students and athletes, between 38 and 45 years of age, were interviewed. Data collection: Individual interviews were conducted with all of the aforementioned study by participants. Data analysis: The interview transcripts were transcribed verbatim and analyzed using thematic analysis procedures guided by the research questions. Findings: The teacher and the coaches indicated that they were better equipped to teach values through PES since their participation in the values training program and were more aware of the importance of having a deliberate approach to ensure that students and athletes develop and transfer values. The teacher and coaches discussed challenges they faced in ensuring the optimal delivery of values education in PES. The students and athletes explained how they learned values by interacting with the teacher and coaches who took part in the program and were able to apply these values in life. The parents also discussed how they observed their children transfer the values learned from PES to the home setting. Conclusion: It is important that teachers and coaches clearly understand the values they are imparting and be well versed in experiential learning approaches for values education, thereby facilitating students' reflection and transfer of values beyond PES. The current findings can inform program developers in and beyond Singapore, demonstrating important elements that contribute to the successful implementation of values within PES programming. However, additional follow-up studies are needed in different contexts to optimize the structuring of PES programming as opportunities to develop citizenship.