Background: The aims of this study were to describe the variations of training monotony (TM), training strain (TS), and acute:chronic workload ratio (ACWR) through Hooper Index categories (fatigue, stress, DOMS, and sleep quality) and to compare those variations between player status and player positions. Methods: Seventeen male professional soccer players participated in this study. Considering player status, participants were divided in nine starters and eight non-starters. Additionally, participants were divided by playing positions: three wide defenders, four central defenders, three wide midfielders, four central midfielders, and three strikers. They were followed during 40-week in-season period. TM, TS, and ACWR were calculated for each HI category, respectively. Data were grouped in 10 mesocycles for further analysis. Results: Results showed variations across the mesocycles. In general, starters showed higher values for TM, TS, and ACWR calculations than non-starters, although there were some exceptions. Regarding player positions, significant differences were found in stress between wide defenders vs central midfielders for TM (p = 0.033, ES = 5.16), central defenders vs wide defenders for ACWR (p = 0.044, ES = 4.95), and in sleep between wide defenders and strikers for TM (p = 0.015, ES = 5.80). Conclusions: This study revealed that an analysis of players’ well-being parameters according to player status and positions can provide clear information to the coaches and their staff to complement the tasks of training monitoring.