Adequate handgrip strength (HGS) is important to safely perform fireground tasks. However, there is limited research describing the deleterious impact of glove use and fatigue from occupational tasks on HGS. Therefore, the aims of this investigation were to quantify the impact of glove use and occupational tasks on HGS, to explore the relationship between HGS versus the glove and task-induced decrement in HGS, and to evaluate the relationship between HGS and decrement in HGS versus occupational performance. Fourteen (Male: n = 13) career structural firefighters (Age: 35.5 ± 7.2 yr) performed a maximal isometric HGS assessment with and without gloves before and immediately following completion of a simulated fireground test (SFGT). General linear model with written contrast was used to identify significant differences in HGS between conditions. Pearson Correlations were used to describe bivariate relationships between the decrements in HGS and occupational task times. Significance was set at p < 0.05. There were significant main effects indicating that gloves, performing occupational tasks, and their combined effects decreased HGS (p < 0.001 for all). There were strong inverse relationships between baseline (barehanded) HGS versus the decrement in HGS from donning gloves (r = -0.82, p < 0.001) and from performing occupational tasks with gloves (r = -0.61, p = 0.021). Baseline HGS and the decrement in HGS due to wearing gloves and performing occupational tasks were not correlated to the timed completion of occupational tasks (p ≥ 0.27). These findings suggest that the use of regulation fire gloves and work-induced fatigue reduces HGS and these decrements are related to HGS. Practitioners are encouraged to utilize training strategies to optimize HGS among structural firefighters.