(1) Background: Leadless pacemakers (LPs) have been proposed as a reimplantation strategy in pacing-dependent patients undergoing cardiac implantable electronic device (CIED) extraction for infection. In this study, we analysed the risk of LP infection when this device is implanted before lead extraction. (2) Methods: This was a retrospective study including patients who underwent LP implantation between 2017 and 2022. Patients were divided in two groups according to whether LP was implanted following CIED extraction for infection (Group 1) or other indications (Group 2). The primary aim was to describe the risk of LP infection. (3) Results: We included in this study 49 patients with a median age of 81 [20–94] years, mostly males (36, 73%). In Group 1 patients, 17 cases (85%) showed systemic CIED infections, and 11 (55%) had positive lead cultures. Most Group 1 cases (n = 14, 70%) underwent one stage of LP implantation and CIED extraction. Mortality rate during follow-up was 20% (nine patients). Patients were followed up for a median of 927 [41–1925], days and no cases of definite or suspected LP infections were identified. (4) Conclusions: The risk of LP infection was extremely low. LP appears as a potential option for reimplantation in this setting and should be considered in pacing-dependent patients at a high risk of CIED infection recurrence.