The purposes of this study were: (i) to analyze the correlation between accumulated workload (AW)—based on season periods—with maturity, linear sprints, maximum oxygen uptake (VO2max), maximum heart rate, and body composition; and (ii) to compare the playing positions based on the mentioned parameters. Twenty-one elite soccer players under the age of 14 participated in the study. They were divided into five groups based on playing positions. The in-season weekly AW was recorded for 26 weeks into two separated periods of 13 weeks (AW-1 and AW-2). Similarly, the following parameters were assessed: body mass, standing and sitting height, body mass index, body fat percentage, maturity offset, age at peak height velocity (PHV), sprinting ability (10 m and 30 m), and VO2max. The main significant differences between playing positions were found for weight, height, sitting height, and sprinting at 10 m and 30 m. No correlation was observed between AW (based on periods) and maturity or between VO2max and AW-2. AW-1 denoted a large positive correlation with AW-2. AW-1 had a moderate negative correlation with VO2max, whereas PHV and maturity presented a strong negative correlation. Young soccer players’ maturity statuses and fitness levels do not imply differences between AW-1 and AW-2. However, the higher the AW in the first half of the season, the higher the AW in the second half. The absence of significant differences between player positions could be associated with the similar training regardless of the playing position. Moreover, soccer positively influences performance in short sprints (10 m), midfielders being the fastest.