In 2018, 1822 incidents relating to death or injury occurred among street cleaners in South Korea. However, South Korea currently lacks comprehensive studies on related injuries based on street cleaners’ job characteristics and environments in the country. This study analyzed injuries according to the job characteristics and environment through a survey of 150 Korean street cleaners working in the Seoul and Gyeonggi-do areas. This study assessed three category measures—demographic, job characteristics, and environments—to determine the effects of injuries. The demographic measures consisted of age, gender, and education level. Job characteristic variables consisted of length of time on the job, job contract, monthly income, working hours per day, working start time, overtime per month, and days off per month. For job environments, this survey included job duty, classification, main tasks, work intensity, and safety equipment. The data were analyzed according to descriptive statistics, injury ratio, and Probit regression analysis. The results of the analysis demonstrated that the participants with the highest risk of injury were mostly males with less than a middle school education. Assessment of the job characteristics showed that the most prevalent length of working experience was less than 5 years, with most engaging in contract/day work. A share of 36.67% of the participants reported injuries. The most prevalent reason for injury was overwork (32.73%), and the most frequent injury area was the lower back (49.09%). In summary, injuries among street cleaners were associated with education level, job experience, days off from work, and work intensity. As such, street cleaners should receive more education to decrease the risk of injuries, regardless of the number of employees or their contract status.