Evaluating force–velocity characteristics on dry-land is of the utmost importance in swimming, because higher levels of these bio-motor abilities positively affect in-water performance. However, the wide range of possible technical specializations presents an opportunity for a more categorized approach that has yet to be seized. Therefore, the aim of this study was to identify feasible differences in maximum force–velocity exertion based on swimmers’ stroke and distance specialization. To this scope, 96 young male swimmers competing at the regional level were divided into 12 groups, one for each stroke (butterfly, backstroke, breaststroke, and front crawl) and distance (50 m, 100 m, and 200 m). They performed two single pull-up tests, 5-min before and after competing in a federal swimming race. We assessed force (N) and velocity (m/s) exertion via linear encoder. There were no significant differences between pre-post maximum force–velocity exertions, despite the decreasing trend. Force-parameters highly correlated with each other and with the swimming performance time. Moreover, both force (t = −3.60, p < 0.001) and velocity (t = −3.90, p < 0.001) were significant predictors of swimming race time. Sprinters (both 50 m and 100 m) of all strokes could exert significantly higher force–velocity compared to 200 m swimmers (e.g., 0.96 ± 0.06 m/s performed by sprinters vs. 0.66 ± 0.03 m/s performed by 200 m swimmers). Moreover, breaststroke sprinters presented significantly lower force–velocity compared to sprinters specialized in the other strokes (e.g., 1047.83 ± 61.33 N performed by breaststroke sprinters vs. 1263.62 ± 161.23 N performed by butterfly sprinters). This study could provide the foundation for future research regarding the role of stroke and distance specializations in modeling swimmers’ force–velocity abilities, thus influencing paramount elements for specific training and improvement towards competitions.