Chronic exertional compartment syndrome (CECS) is one of the recalcitrant overuse injuries of the legs. CECS is traditionally diagnosed with an intracompartmental pressure measurement (ICPM). The primary objective of this article was to report the relationship between exertional compartment pain and intracompartmental pressure in young service members. This study is a descriptive analysis of patient records from a central military hospital from 2013 to 2016 (study design: historic cohort; level of evidence, 3). A total of 573 young service members with exercise-related leg pain were evaluated. An ICPM of at least one muscular compartment was performed in 501 patients (87%) 1 min after a standardized running test. CECS (32%), medial tibial stress syndrome (MTSS) + CECS (27%), and MTSS (21%) were the most common diagnoses. In the CECS category, most patients (68%) had ICPM values >35 mm Hg in both anterior and deep posterior compartments, 22% had isolated CECS of the anterior compartments, and the others had combinations of pressures >35 mm Hg in one or more of the four leg compartments (9%). Comparison of exertional pain scores with the ICPM showed a negligible correlation for the anterior compartments (Spearman rank correlation coefficient = 0.257, confidence interval = 0.191–0.327). Service members rated needle pain of the ICPM procedure as moderate: median pain rating 5 out of 10 (range 1–10). This score did not significantly differ between men and women (P = 0.409) and was not different if only anterior compartment versus multiple compartments were measured (P = 0.236). There is a negligible correlation between exertional compartment pain level and intracompartmental pressure in the leg. Current advice to avoid or minimize ICPM due to needle pain concerns does not appear warranted.