The 2021 ESC/EACTS guidelines recommend percutaneous approaches for failing bioprostheses. These methods are less invasive, resulting in shorter recovery times and fewer complications. Valve-in-valve (ViV) procedures offer a promising solution, although simultaneous transcatheter replacement of two valves (double ViV) still needs to be standard and primarily documented through case reports. This case series presents the initial outcomes of two patients who underwent simultaneous double transcatheter heart valve implantation, exploring the feasibility of this approach in the elderly. As the demand for bioprosthetic valves grows, innovative strategies like double ViV may provide valuable solutions to address valve degeneration and enhance patient outcomes.