Purpose To describe the functional and anatomical results of complicated retinal detachment (RD) treated with small-gauge pars plana vitrectomy (PPV) and combined perfluorodecalin and polydimethylsiloxane tamponade (double filling, DF). Methods Retrospective analysis of consecutive patients with complex RD (severe proliferative vitreoretinopathy, inferior/posterior/giant retinal tears, and traumatic detachments) treated with small-gauge PPV, membrane peeling, and DF at the Department of Ophthalmology at San Gerardo Hospital, Monza, Italy. Main outcome measures included best-corrected visual acuity (BCVA), rates of retinal reattachment, and complications. Results This study included 15 patients with a median follow-up (FU) of 6 months (range 1–22). Three patients with early retinal redetachment under tamponade and FU shorter than 3 months were excluded from the final functional analysis, but they were considered anatomical failure. At the last examination, BCVA improved in 50% of patients and remained stable in 25% of patients and anatomical success was achieved in 73% of eyes, 64% of them without any endotamponade. Three eyes had retinal redetachment after perfluorodecalin/silicone oil exchange because of diffuse proliferative vitreoretinopathy (PVR) and required reoperation to achieve retinal attachment. In eyes with anatomical success, macular pucker was the most frequent long-term complication (27%). Conclusion In the management of complex RD, small-gauge pars plana vitrectomy, and double filling endotamponade using wide-angle viewing systems was a well-tolerated and effective technique to preserve visual acuity and achieve anatomical success.