(1) Background: The objective of this research was to analyse the most demanding passages (MDP) considering the sprint variable relative to the maximum level of sprint ability of each player as a function of player position, final outcome and part of the match during the competitive phase of a professional soccer season. (2) Methods: Global positioning system (GPS) data were collected from 22 players according to their playing position in the last 19 match days of the Spanish La Liga professional soccer in the 2020/2021 season. MDP were calculated from 80% of the maximum sprint speed of each player. (3) Results: Wide midfielders covered the greatest distance at >80% of the maximum speed (2.4 ± 1.63 seg) and the longest duration (21.91 ± 13.35 m) in their MDP. When the whole team was losing, it demonstrated greater distances (20.23 ± 13.04 m) and longer durations (2.24 ± 1.58 seg) compared to games in which it was winning. When the team ended up drawing, the relative sprint distance covered in the second half was significantly greater than in the first (16.12 ± 21.02; SD = 0.26 ± 0.28 (−0.03/−0.54). (4) Conclusions: Different demands of MDP, according to the sprint variable relative to the maximum individual capacity in competition, are required when contextual game factors are considered.