Background/Objectives: A disadvantage of Descemet stripping automated endothelial keratoplasty (DSAEK) in eyes with prior glaucoma filtration surgery is the difficulty in maintaining air tamponade during the procedure. Herein, we report the use of bleb compressive sutures in managing air tamponade in the anterior chamber during DSAEK in eyes with blebs following trabeculectomy. Methods: This retrospective case series included 34 eyes of 33 patients that developed bullous keratopathy following trabeculectomy. Bleb compression suturing was performed using a10-0 nylon suture in eyes with an intraocular pressure (IOP) < 10 mmHg or a fragile ischemic bleb. Postoperative IOP, air ingress into the bleb, rebubbling, bleb leakage, and bleb damage were evaluated. Results: Of the 34 eyes, 13 underwent bleb compression suturing before DSAEK (suture group), whereas 21 eyes did not (non-suture group). Mean preoperative IOP was lower in the suture group than in the non-suture group, whereas postoperative IOP at 2 h was similar. Preoperative to 2-h postoperative IOP increased by 18±9.3 and 11.7±3.1 mmHg in the suture and non-suture groups, respectively, with no significant differences. At 2-h postoperatively, two eyes in the suture group and one eye in the non-suture group exhibited an IOP spike (≥30 mmHg). One eye in the non-suture group required rebubbling owing to air ingress into the bleb. Postoperatively (1–2 weeks), the mean IOP was 7.1±3.2 and 9.4±4.6 mmHg in the suture and non-suture groups, respectively. Preoperative and postoperative IOP did not significantly differ in either group. No suture-related complications were observed. Conclusion: In DSAEK for eyes with bleb, bleb compression suturing provides effective air tamponade during graft adhesion.