We sought to refine understanding about associations identified in prior studies between angiotensin‐II receptor blockers, metformin, selective serotonin reuptake inhibitors, fibric‐acid derivatives, or calcium channel blockers and progression to glaucoma filtration surgery for open‐angle glaucoma (OAG). We used new‐initiator, active‐comparator cohort designs to investigate these drugs in two data sources. We adjusted for confounders using stabilized inverse‐probability‐of‐treatment weights and evaluated results using “intention‐to‐treat” and “as‐treated” follow‐up approaches. In both data sources, Kaplan–Meier curves showed trends for more rapid progression to glaucoma filtration surgery in patients taking calcium channel blockers compared with thiazides with as‐treated (MarketScan P = 0.15; Medicare P = 0.03) and intention‐to‐treat follow‐up (MarketScan P < 0.01; Medicare P = 0.10). There was suggestion of delayed progression for selective serotonin reuptake inhibitor compared with tricyclic antidepressants in Medicare, which was not observed in MarketScan. Our study provided support for a relationship between calcium channel blockers and OAG progression but not for other investigated drugs.