Background and objective Despite ongoing efforts to increase diversity in the field, orthopaedic surgery continues to be the least diverse specialty in all of medicine. This study aimed to assess experiences in medical school and their impact on the decision to pursue orthopaedic surgery residency, and specifically, if these experiences varied by race, including underrepresented minority (URM), or gender. We hypothesized that male and Caucasian residents would report earlier exposure to orthopaedics and mentorship, contributing to earlier decisions to pursue the field. Methods A voluntary survey assessing factors influencing the decision to pursue orthopaedic surgery was sent to 2,122 orthopaedic surgery residents. We compared differences in response between male and female genders as well as three different racial groups (URM, Asian, and Caucasian). Differences in ordinal variables between independent groups were compared using independent t-tests for normally distributed data and Mann-Whitney U tests for non-normally distributed data. Differences in categorical data were analyzed using the χ2 test or Fisher's exact test as appropriate. Results A total of 337 residents completed the survey, yielding a response rate of 15.9%. Males were more likely than females to agree that a role model or mentor of the same sex and race positively influenced their decision [median interquartile range: (IQR): 4 (2-5) vs. 2 (2-4); Mann-Whitney U=8807, p<0.001, r=0.32] and were more likely to disagree they experienced gender-based discrimination [1 (1-2) vs. 3 (2-4); U=7834, p<0.001, r=0.38). Interest in orthopaedics before medical school was higher in males (n=145, 64.7%) than females (n=56, 49.6%), while 15.0% (n=17) of females became interested during elective rotations compared to 7.1% (n=16) of males [χ²(3, N=337)=9.10, p=0.028, V=0.16]. More Caucasian residents (n=166, 64.3%) became interested in orthopaedic surgery before medical school compared to URM (n=22, 57.9%) and Asian (n=13, 31.7%) residents, while 7.7% (n=20) of Caucasians became interested during elective rotations compared to 12.2% (n=5) of Asians and 21.0% (n=8) of URM residents [χ²(6, N=337)=25.11, p<0.001, V=0.22]. Conclusions There are several significant differences in the experiences of female and URM medical students who chose to pursue orthopaedic surgery relative to male and Caucasian students. The low response rate may reflect self-selection bias and should be taken into account when interpreting these findings.