Background: Few previous studies have analyzed the effects of certain specific static and dynamic warm-up components on recreational sports players with a previous hamstring injury. Therefore, the aim of this study was to analyze changes in some modifiable and external risk factors after (immediately and in a follow-up assessment after 10 min) a static or dynamic warm-up program on recreational sports players with a previous hamstring injury. Methods: A total of 62 participants were randomized into 2 groups: static warm-up (SW) (n = 31) or dynamic warm-up (DW) (n = 31). Range of movement (RoM), perceived pain, the pressure–pain threshold, and joint position sense were assessed at baseline, immediately after the intervention and 10 min afterwards. The intervention for the SW (hot pack procedures in both hamstring muscles) lasted 20 min. The DW intervention consisted of a running exercise performed on a treadmill for 10 min. Results: Both groups showed statistically significant changes (p ≤ 0.05) in the primary outcomes (perceived pain and the pressure–pain threshold) at the three measurement times (this was also true for RoM for the SW group, with statistically significant differences only between times from the baseline to the 10-min follow-up; p ≤ 0.05, d = 0.23). The intra-group secondary outcome showed no statistically significant changes (p > 0.05) in both groups (except for the period from the baseline–immediately after in the DW group; p ≤ 0.05, d = 0.53). The comparison between groups showed no statistically significant differences for any of the variables analyzed. (p ≥ 0.05). Conclusion: The present findings suggest that both specific warm-up modalities seem to positively influence perceived pain on stretching and the pressure threshold; however, the significant reduction in the joint repositioning error and the larger effect sizes observed in the DW group suggest that this method has a greater beneficial impact in recreational sports players with clinical histories of hamstring injuries.