Robotic assembly remains a significant challenge due to complexities in visual perception, functional grasping, contact-rich manipulation, and performing high-precision tasks. Simulation-based learning and sim-to-real transfer have led to recent success in solving assembly tasks in the presence of object pose variation, perception noise, and control error; however, the development of a generalist (i.e., multi-task) agent for a broad range of assembly tasks has been limited by the need to manually curate assembly assets, which greatly constrains the number and diversity of assembly problems that can be used for policy learning. Inspired by recent success of using generative AI to scale up robot learning, we propose MatchMaker, a pipeline to automatically generate diverse, simulation-compatible assembly asset pairs to facilitate learning assembly skills. Specifically, MatchMaker can 1) take a simulation-incompatible, interpenetrating asset pair as input, and automatically convert it into a simulation-compatible, interpenetration-free pair, 2) take an arbitrary single asset as input, and generate a geometrically-mating asset to create an asset pair, 3) automatically erode contact surfaces from (1) or (2) according to a user-specified clearance parameter to generate realistic parts. We demonstrate that data generated by MatchMaker outperforms previous work in terms of diversity and effectiveness for downstream assembly skill learning. For videos and additional details, please see our project website: https://wangyian-me.github.io/MatchMaker/.