With the increasing popularity of pickleball (PB) has come an increase in upper extremity (UE) injury. This study examines the relationship between PB-related UE injury and player characteristics, typical weekly playing behavior, grip tightness, and stretching or strengthening exercise among recreational PB players. Players at least 18 years of age who played PB for at least six months were recruited to complete an anonymous online survey. Among the 253 participants, 41% reported at least one UE injury: 10% acute and 37.5% chronic. Chi-square analysis (α = 0.05) was used to determine between group differences. The risk of UE injury was 1.51 to 1.53 times higher among individuals who played longer or more frequent sessions or played on consecutive days. Acute injury was more likely in those who played >two hours at a time, on consecutive days, or maintained a tight baseline grip-with relative risks of 2.38, 4.97, and 2.67, respectively. Chronic injury was more common in those who played >two years, at higher skill level, or >six hours a week. No difference in UE injury and sex, strengthening, or stretching was found. The risk of UE injury was higher for those who play longer, more frequently, or on consecutive days. Additionally, acute injury was more likely when using a tight grip for baseline shots and chronic injury was more common among those who played more years, at a higher skill level, or greater playing volume.