Background: Street workout (SW) is an urban sport based on calisthenic exercises. Injury profiles and risk factors are widely explored in various sport disciplines. However, because of the lack of research in SW, injury profiles have not yet been established. Purpose: To investigate the characteristics and prevalence of injuries and variables that may increase these odds in SW practitioners. Study Design: Case-control study; Level of evidence, 4. Methods: An electronic survey was conducted between September 2018 and March 2019 in order to obtain practitioner information, physical activity level, training characteristics, and injury information of SW practitioners. Responses from 93 practitioners were eligible for analysis. Univariate and multivariate binary logistic regression analyses were used to examine the association among several variables and the presence of injury in the past 12 months based on odds ratios (ORs). Results: Overall, 62.4% of the 93 participants reported an injury in the previous 12 months, and tendinopathy was the most reported diagnosis (31.0% of injured practitioners). High injury frequency was reported in the shoulder (23.0%) and back (upper and mid) (18.4%). Overtraining was the most reported perception of cause of injury (56.9%). Most injured practitioners (20.7%) performed freestyle exercises before the injury, followed by upper body exercises. A history of previous injuries (OR, 4.078; P = .005) and the middle and higher tertiles of vigorous physical activity (OR, 4.370; P = .015 and OR, 5.634; P = .003, respectively) were associated with a higher odds of injury. Conclusion: In SW, the shoulder and back (upper and mid) were the most injured body parts, with tendinopathy being the most frequent diagnosis. Overtraining was typically reported as the perceived cause of injury, with freestyle and upper limb exercises the most performed exercises when injured. A history of previous injuries, along with vigorous physical activity, was found to augment the odds of injury. More research is needed to corroborate our findings, along with increased knowledge about SW practice and injuries.