Introduction: This article reports a case of ocular perforation during a retrobulbar block in a patient who underwent scleral buckle for retinal detachment. Methods: Sterile air was immediately injected into the vitreous cavity to restore intraocular pressure and the scleral buckle operation was quickly finished. One week later, a laser retinopexy was performed on the two retinal holes that were outside the foveal area. After 6 months, spectral domain–optical coherence tomography and optical coherence tomography angiography were performed on the perforated wall centered on the exit hole area. Results: The visual acuity was maintained 20/20 and the retina was totally attached. Spectral domain–optical coherence tomography showed a localized interruption of inner retina, retinal pigment epithelium, and choroid, with a higher posterior reflectivity in correspondence with the sclera. Optical coherence tomography angiography was able to detect atrophic alterations in the choroidal slab with a good visualization of large and rarefied choroidal vessels due to lack of retinal pigment epithelium and choriocapillaris. Conclusion: When ocular perforation by a needle is outside the foveal area and when there is an early awareness of the perforation, the complications may be avoided, and we could observe a good final visual acuity result. Furthermore, using spectral domain–optical coherence tomography and optical coherence tomography angiography, we could observe the perforated eyeball wall and study the effects of a 25-gauge needle perforation in the retinal and choroidal blood stream.