To evaluate the outcomes of Descemet membrane endothelial keratoplasty (DMEK) and Descemet's stripping endothelial keratoplasty (DSEK) in eyes with prior glaucoma surgery. Design; Case-matched retrospective comparative case series.Setting / Study Population: Forty-six DMEK procedures were matched with 46 DSEK procedures at a single institution.Cases were matched based on preoperative visual acuity, lens status and surgical indication.The outcome measures included visual acuity improvement, primary and secondary graft failure, endothelial rejection, intraocular pressure (IOP) elevation, and the need for additional glaucoma intervention.Best-corrected visual acuity (BCVA) improved by -0.89 LogMar in the DMEK group and -0.62 LogMar in the DSEK group (p=0.005) at one year follow up. Visual acuity was significantly better in the DMEK group at post-operative months 1, 3, 12, and at last follow up. The percentage of patients achieving 20/40 or better BCVA was higher in the DMEK group at all time points, notably 47% in the DMEK group vs 15% in the DSEK group at 1 year (p=0.002). Secondary graft failure was lower in the DMEK group (DMEK 0% vs DSEK 17%, p=0.006). Primary graft failure rate and air injection rate were similar. There were no differences in the rate of post-operative IOP elevation or in the need for additional glaucoma intervention.In complex eyes with prior glaucoma surgery, DMEK offers faster visual recovery, better final visual acuity, and a lower rate of secondary graft failure compared with DSEK during the first postoperative year and beyond.