A growing appreciation of the potential benefits of experimentation to tame the complexities of urban transformation has led to an increase in related research activity. Building on a “practice-to-policy” experimentation-based framework, this paper investigates the adaptive policymaking process for urban regeneration in Shenzhen since the 2000s. It finds that “explorative experimentation” is used to identify a general direction in the absence of a clear route for the policy process, while “generative experimentation” is sequentially dedicated to specific issues for the improvement of the entire policy package within a particular reform. We argue that understanding the successive roles or hybrid functions of these two types of experiment adds new insights to the development rationales for Shenzhen's urban regeneration and provides inspiration for an experimental model of urban governance. Governments and policymakers can benefit from the experimentation-based approach, as presented in the Shenzhen case, to pursue policy innovation embedded in local contexts.