Background: Global positioning system (GPS) based player movement tracking data are widely used by professional football (soccer) clubs and academies to provide insight into activity demands during training and competitive matches. However, the use of movement tracking data to inform the design of training programmes is still an open research question. Objectives: The objective of this study is to analyse player tracking data to understand activity level differences between training and match sessions, with respect to different playing positions. Methods: This study analyses the per-session summary of historical movement data collected through GPS tracking to profile high-speed running activity as well as distance covered during training sessions as a whole and competitive matches. We utilise 20,913 data points collected from 53 football players aged between 18 and 23 at an elite football academy across four full seasons (2014–2018). Through ANOVA analysis and probability distribution analysis, we compare the activity demands, measured by the number of high-speed runs, the amount of high-speed distance, and distance covered by players in key playing positions, such as Central Midfielders, Full Backs, and Centre Forwards. Results and Implications: While there are significant positional differences in physical activity demands during competitive matches, the physical activity levels during training sessions do not show positional variations. In matches, the Centre Forwards face the highest demand for High Speed Runs (HSRs), compared to Central Midfielders and Full Backs. However, on average the Central Midfielders tend to cover more distance than Centre Forwards and Full Backs. An increase in high-speed work demand in matches and training over the past four seasons, also shown by a gradual change in the extreme values of high-speed running activity, was also found. This large-scale, longitudinal study makes an important contribution to the literature, providing novel insights from an elite performance environment about the relationship between player activity levels during training and match play, and how these vary by playing position.