We report successful outcome of a huge post- trabeculectomy intra-bleb hematoma and hyphema that occurred following digital ocular compression. The patient was a 64-year-old lady suffering from bilateral primary angle closure glaucoma and cataract. She was on anti-platelet therapy. She underwent single-site phacoemulsification, intra-ocular lens implantation and trabeculectomy with mitomycin C in the right eye. The trabeculectomy was under-filtering. She was asked to perform digital ocular compression thrice daily. On 15(th) post-operative day, she presented with a huge intra-bleb hematoma and hyphema. The hematoma did not respond to conservative measures and was drained to prevent bleb failure. We recommend caution in the consideration of digital ocular compression in patients on prophylactic anti-coagulation.