Background: Sport Education has a dual interest in promoting active student engagement in games and improvements in their game-play. However, very few studies have concurrently examined how learners' game-play development is influenced by cognitive, social, and situated constraints, especially over consecutive Sport Education seasons. Purpose: The purposes of this study were threefold: (i) to concurrently examine the evolution of students' game-play participation and performance; (ii) to examine the transfer of game-play configurations across three seasons of invasion games; and (iii) to investigate how students' game-play development was influenced by various situational constraints (e.g. nature of instruction, student engagement in instructional processes, and modifications imposed on the game forms). Participants and setting: The participants were 26 seventh-grade students (10 girls and 16 boys, mean age 12.3) from a middle school in northern Portugal. Students participated in three consecutive Sport Education seasons of basketball (19 × 45-minute lessons), handball (12 × 45-minute lessons), and football (16 × 45-minute lessons). Team membership remained the same throughout the three seasons. Two teams of five players (mean age 12.2), who played three-a-side games in every initial and final lesson of each season were sampled for game-play tracking across the three seasons. Methods: Digital video records were taken of 53 lessons. Pre-test to post-test quantitative measures were conducted on students' game involvement (sum of total game actions) and performance (decision-making, skill-execution, and efficacy). Descriptive narratives of play were created to capture the effects of contextual circumstances on participants' game-play behaviours and the evolution of their prototypical configurations of play. A field diary provided a chronological matrix of the principal instructional strategies and the instructional responsibility taken up by the teacher and students during the seasons. On-going student team interviews were conducted to gather learners' perceptions of how situational constraints influenced their game-play development. Findings: The narratives of play showed a noticeable evolution in the quality of players' game-play configurations over time. The progress in students' ability to play invasion games was influenced by an interdependent relationship between the nature of the instructional processes used, the level of cognitive and social engagement of students with the subject matter, and specific constraints imposed on the game forms (level of defensive pressure, the dimension of the field). Conclusions: Although most research in Sport Education has shown a positive trend of student game-play development, this study revealed that the evolution of game involvement and performance is neither linear nor concurrent. Both game-play development and the transfer of tactical solutions and decision-making processes across games within the same category were critically and differentially influenced by various situational constraints.