Background: Research indicates that mechanics differ between athletes with and without upper extremity pain; however, it is unclear which modifiable risk factors exist for throwing-related pain in softball athletes. Purpose: To determine whether sport specialization, throwing, practice, and strength and conditioning training volumes vary between youth softball athletes with and without upper extremity pain. It was hypothesized that youth softball athletes with upper extremity pain would participate in softball year-round and have greater throwing, practice, and strength and conditioning volumes compared with those without pain. Study Design: Cross-sectional study; Level of evidence, 3. Methods: A total of 232 youth softball athletes from travel ball, middle school, and high school leagues were invited to complete a survey to assess pain, sport specialization, throwing, practice, and strength and conditioning training volumes. Participants were classified into upper extremity pain and no pain groups based on their survey answers. The responses were compared between groups using Mann-Whitney U and chi-square tests. Results: A total of 101 athletes—with a mean ± SD age of 13.3 ± 2.3 years, height of 161 ± 13.4 cm, and weight of 59.8 ± 14.8 kg—completed the survey and were included for analysis. The response rate was 43.53%, with 22 athletes in the upper extremity pain group and 79 athletes in the no pain group. A significant difference was observed between hours devoted per week to off-season softball practice ( U, 626.6; Z =–2; P = .045), where those without upper extremity pain spent 4 fewer median hours (6 hours) practicing softball per week in the off-season compared with those with pain (10 hours). Also, a significant difference was found between the number of throws during an in-season game ( U, 457; Z, –2.28; P = .022), where those without upper extremity pain reported 21 fewer median throws (70 throws) during an in-season game compared with those with pain (91 throws). Furthermore, 77% of those who reported upper extremity pain continued to play despite their pain. There were no other significant differences between demographic characteristics, specialization, injury history, and primary position, as well as throwing, practice, and strength and conditioning volumes. Conclusion: Our study demonstrates that youth softball athletes with upper extremity pain had more throws during in-season games and increased hours per week devoted to off-season practice than athletes without upper extremity pain. Our findings support the need for softball stakeholders (eg, coaches, clinicians, parents, and administrators) to engage in further research and recommendations regarding in-season pitch counts and off-season rest.