This study aimed to investigate: i) how Small-Sided and Conditioned Games based on different representation and exaggeration modification strategies, from the Teaching Games for Understanding pedagogical principles, affected team performance and exploratory behaviour; and ii) how teams and players of different ages and skill levels were affected by the use of these different modification strategies. In total, forty-eight youth male soccer players participated in the study (U15, n = 24 mean age = 13.06 +/- 1.53 years; U17, n = 24 mean age = 16.89 +/- 0.11 years). In both categories, players were organized into three groups according to their tactical efficiency level (Group 01 = High Skilled Players (HSP), Group 02 = Intermediate Skilled Players (ISP), and Group 03 = Low Skilled Players (LSP)). The HSP and LSP groups performed two types of Gk+4vs4+Gk Small-Sided and Conditioned Games (SSCGs) based on different representation and exaggeration modification strategies. The first type of SSCGs was modified by structural constraints (Structural SSCG) and the second type was modified by rule manipulation (Manipulation SSCG). Team performance and exploratory behaviour were analysed through the Offensive Sequences Characterization System and Lag Sequential Analysis, respectively. SSCG modification strategies affected differently tactical performance and exploratory behaviour of teams composed of players of different skill levels. It was found that SSCG modification strategy through rule manipulation provided players and teams with a higher level of difficulty, compromising their performance and inhibiting exploratory behaviour. This information is crucial to practitioners wishing to apply more appropriate pedagogical strategies to improve a specific tactical problem using a player-centred and game-based approach.