Objectives This study investigated whether exercising with different relative loads would be associated with different experienced pain intensities in individuals with patellar tendinopathy. Materials and Methods We recruited 14 individuals with patellar tendinopathy for this randomized crossover study. In a randomized order, participants performed one set of single-legged leg presses during one session with three relative loads (6 repetition maximum (RM), 10RM, and 14RM). The primary outcome was pain during exercise measured on a 0–10 Numerical Rating Scale (NRS) (0 = no pain, 10 = worst pain), which participants rated after performing the exercise set with each relative load. Results No differences in pain during either of the three relative loads were observed (F(2, 26) = 0.06, p = 0.942). The participants’ experienced pain was 4.5 NRS (SD1.7), 4.5 NRS (SD1.7), and 4.6 NRS (SD2.0) during the 6RM, 10RM, and 14RM loads, respectively. A secondary analysis revealed no statistically significant difference in pain intensity between the performance of the first, second, or third exercise set regardless of the load (F(2, 26) = 1.06, p = 0.367). Conclusions There was no difference in pain intensity during either relative load among individuals with patellar tendinopathy. Therefore, higher loads may be applied, associated with enhanced tendon adaptation.