Excessive daily training load (TL) can affect the musculoskeletal system health of youth elite soccer players. The purposes of this study were (i) to describe the TL and session rating of perceived exertion (s-RPE) throughout the competition season; (ii) to analyze the weekly (w) differences of acute (daily) workload (wAWL), chronic workload (wCWL), acute–chronic workload ratio, training monotony (wTM), and training strain (wTS) among three periods over the season (early-, mid-, and end-season) by playing position; and (iii) to compare the TL variables during competition periods for the whole team. Twenty young elite soccer players in the under-14 category participated in this study. The game positions were considered as six wide defenders and wide midfielders (WM), five central defenders and central midfielders, and four strikers (ST). Daily monitoring was continued for 26 weeks during a full competition season. According to the league schedule, the season was divided into three periods: early-season from w1 to w8, mid-season from w9 to w17, and end-season from w18 to w26. The main results were that the higher TLs were detected in the early- and mid-season. There was a wAWL and wCWL decrease for all playing positions from early- to mid- and end-season, but the wCWL change was significant only from early- to mid-season (p ≤ 0.05). For all playing positions but ST, there was a considerable wTM increase from early- to mid-season. When compared with all other playing positions in terms of wAWL and wCWL, WM showed significantly greater values (p ≤ 0.05). Throughout the season periods, all workload indicators showed a considerable reduction, although there was a significant increase in the three other workload-derived variables (all with p ≤ 0.05) and namely: (i) wACWLR from mid- to end-season; (ii) wTM from early- to mid- and end-season; and (iii) wTS from early- to mid-season. Daily training load and s-RPE had significant fluctuations during all macrocycles of the competition season (p ≤ 0.05). In addition, in the mid-season, wTM and wTS were higher. Training load monitoring (in terms of, e.g., wAWL, wCWL, and s-RPE) could be the key for coaches of soccer teams to prevent overtraining and injury, especially in U-14 players, who are more susceptible to being affected by high workload.