(1) Background: There is a lack of literature that examines the impact of early vs. late sport specialization on quality of life after retirement from tennis. Thus, the purpose of this study was to examine the relationship between early specialization in the sport of tennis and health outcomes after retirement from collegiate/professional sport; (2) Methods: Participants were recruited through social media posts, newsletters, and contacts with tennis organizations. Basic demographic and injury information was collected from 157 former tennis players, along with the age of tennis specialization and two questionnaires: the Oslo Sports Trauma Research Center Questionnaire on Health Problems (OSTRC), and the CDC HRQOL-14 “Healthy Days Measure” Questionnaire (HRQOL); (3) Results: Significant differences (F1,117= 5.160,p< 0.025) in the specialization age between the low (11.9 ± 4.5 y) and high (9.8 ± 4.1 y) OSTRC groups were found after covarying for the current age. No difference (F1,72= 0.676,p< 0.414) was shown among the high (10.9 ± 4.4 y) and low (11.28 ± 4.6 y) HRQOL groups for the specialization age after covarying for the current age. A weak negative correlation was identified between the OSTRC score and specialization age (r = −0.233,p= 0.008), while no significant changes were shown between the specialization age and HRQOL score (r = −0.021,p= 0.857), or between the OSTRC and HRQOL scores (r = 0.146,p= 0.208); (4) Conclusions: Retired tennis players with low injury/illness severity scores specialized in tennis later than those with high injury/illness severity scores, while no differences in the specialization age were noted when the sample was separated into HRQOL groups.