Collusive bidding has been a deep-seated issue in the construction market for a long time. The strategies implemented by bid riggers are deliberate, interactive, and complex, suggesting that antitrust authorities have difficulty preventing collusive behaviors. Based on game payoff matrixes, this study proposes a system dynamics (SD) model to present the deterrence of punitive measures, namely the certainty of punishment (CoP) and the severity of punishment (SoP), on regular bidders’ to-collude decision-making. Data were collected from the Chinese construction industry to test the proposed SD model. While the model was supported, the results indicate that the CoP has a greater impact than the SoP on deterring regular bidders from making to-collude decisions. Furthermore, these two punitive measures cannot be replaced by each other, given the same deterrence effects. Thus, the study demonstrates the usefulness of deterrence theory to inhibit collusive bidding in the construction sector. It also sheds some light on the formulation of competition policy from the perspective of deterrence.