Purpose: The purposes of this study were to (1) analyze the variations of acute and chronic training load and well-being measures during 3 periods of the season (early, mid, and end) and (2) test the associations between weekly training load and well-being measures during different periods of the season. Methods: Thirteen professional volleyball players from a team competing in the Portuguese Volleyball First Division (age 31.0 [5.0] y) were monitored during an entire season. Weekly acute (wAL) and chronic load (wCL), acute to chronic workload ratio (wACWL), and training monotony (wTM) were calculated during all weeks of the season. The weekly values of muscle soreness (wDOMS), stress (wStress), fatigue (wFatigue), sleep (wSleep), and Hooper index (wHI) were also obtained across the season. Results: The midseason had meaningfully low values of wAL (−26.9%; effect size [ES]: −1.12) and wCL (−28.0%; ES: −2.81), and greater values of wACWL (+38.9%; ES: 2.81) compared with early season. The wCL (+10.6%; ES: 0.99), wStress (44.6%; ES: 0.87), and wHI (29.0%; ES: 0.62) were meaningfully greater during the end of season than in midseason. Overall, wAL presented very large correlations with wDOMS (r = .80), wSleep (r = .72), and wFatigue (r = .82). Conclusions: The results of this study suggest that the load was meaningfully higher during early season; however, stress was higher during the final stages of the season. Overall, it was also found that the acute load is more highly correlated with well-being status and its variations than chronic load or training monotony.