In this study, we aimed to identify the time course effects of different intensities of static stretch (SST) (maximal intensity without pain vs. high-intensity with moderate pain) on flexibility. This study included 16 healthy students (8 men and 8 women) who performed 1) 5-minute SST at 100%, 2) 110%, and 3) 120% intensity, as well as 4) no stretching (control) in a random sequence on four separate days. Static passive torque (SPT), hamstring electromyography (EMG), and pain intensity were continuously recorded during SST. We assessed markers of stiffness, range of motion (ROM), and maximal dynamic passive torque (DPTmax) before SST and 0, 15, 30, 45, 60, 75, and 90 minutes after SST. Stiffness decreased and ROM and DPTmax increased significantly immediately after SST at the three different intensity levels (p < 0.05). The effects of SST at 120% intensity were stronger and lasted longer than the effects of SST at 110% and 100% intensity (stiffness: -17%, -9%, and -7%, respectively; ROM: 14%, 10%, and 6%, respectively; DPTmax: 15%, 15%, and 9%, respectively). SPT decreased after SST at all intensities (p < 0.05). SST at 120% intensity caused a significantly greater reduction in SPT than SST at 100% intensity (p < 0.05). Pain intensity and EMG activity increased immediately after the onset of SST at 120% intensity (p < 0.05), although these responses were attenuated over time. Stretching intensity significantly correlated with the degree of change in ROM and stiffness (p < 0.05). These results support our hypothesis that stretch-induced flexibility is amplified and prolonged with an increase in stretch intensity beyond the pain threshold. Additional studies with more participants and different demographics are necessary to examine the generalizability of these findings.