Purpose: To evaluate the clinical presentation, management, and outcome of eyes with an inadvertent globe perforation during peribulbar or retrobulbar block. Methods: This retrospective study evaluated the eyes which had an accidental globe perforation during local ocular anesthesia from 2012 to 2020. The patients were divided into three groups: group 1, Clear media with no rhegmatogenous retinal detachment (RRD); group 2, significant vitreous hemorrhage (VH) precluding the retinal view without RRD; and group 3, RRD with/without VH. Results: Twenty-five patients were included in the study. The mean axial length (AL) was 24.7 ± 2.7 mm (range, 20.9–31.2 mm). The most common presenting feature was VH (n = 14). The treatment included retinal laser barrage (n = 7) and vitrectomy (n = 17). Retinal breaks were identified in all the eyes (total breaks = 37). The mean presenting best-corrected visual acuity in groups 1, 2, and 3 were logarithm of the minimum angle of resolution 0.79 ± 0.73, 1.82 ± 0.78, and 2.13 ± 0.59 respectively. All the treated patients had an attached retina at the last follow-up. The mean final best-corrected visual acuity for each group was logarithm of the minimum angle of resolution 0.59 ± 0.79, 0.48 ± 0.26, and 1.25 ± 0.64, respectively (p = 0.006). The development of RRD was associated with a larger AL (p = 0.015); while the development of significant VH associated with the superior location of the perforation (p = 0.015), late recognition of the perforation (p = 0.004), and multiple perforations (p = 0.015). Conclusions Early recognition and intervention in eyes with an inadvertent perforation can lead to a good outcome. Eyes with a longer AL, superior, and multiple perforations are at higher risk of developing complications like RRD and VH. Complications like RRD, macular injury, and vascular occlusion are risk factors for poor prognosis.