Occupational health and safety (OHS) laws are not always abreast of their times in developing countries. Thus, complying with OHS laws might be considered to be pedantic and superficial by contractors. In addition to meeting legislative requirements, evidence suggests South African contractors also self-regulate, and this further affects their health and safety performance beyond the remit of legislative guidelines. However, what do a commitment to self-regulation and the transition between self-regulation and compliance with OHS regulations entail in a typical construction company in South Africa? In this study the various levels of self-regulation and compliance to OHS legislative requirements in South Africa have been examined and how these affect the number of accidents on construction sites. The aim of this chapter is to answer the research question using a 20-item scale to develop a conceptual framework that helps to explain the relationship between contractors’ commitment to a work-safety culture, self-regulation and accident frequency rates (AFRs). From the study, it was found that there is a high level of self-regulation ranging from 65% to 97%, and an average AFR of 1.02 accidents per 100,000 hours in South Africa. It also emerged that there is a significant, negative, linear relationship between the level of contractor self-regulation and AFR. It is concluded that the more contractors self-regulate, the lower their AFR. It is recommended that public and private sector clients encourage the use of voluntary self-regulation towards strengthening contracting organisations’ ability to prevent accidents on construction sites.