(1) Objectives: This study evaluated the clinical outcomes of dental implants placed in previously failed sites and discussed the risk factors that mattered in reimplantation. (2) Methods: All the cases by one specific implantologist during his first five years of clinical practice were screened, with a focus on those who received reimplantation. The clinical outcomes were assessed, including the implant survival, peri-implant health, and patients’ satisfaction. (3) Results: 28 patients (31 implants) were recorded as failures from 847 patients (1269 implants), with a 2.4% overall failure rate at the implant level, of whom 19 patients (21 implants) received reimplantation treatment. After a mean follow-up of 33.7 ± 10.1 months (95% CI 29.1–38.3 months), 20 implants remained functional, but 1 implant revealed a secondary early failure, indicating a 95.2% overall survival rate. The mean probing depth (PD), modified sulcus bleeding index (mSBI), and marginal bone loss (MBL) of the surviving reinserted implants were 2.7 ± 0.6 mm (95% CI 2.5–3.0 mm), 0.7 ± 0.5 (95% CI 0.5–1.0), and 0.5 ± 0.6 mm (95% CI 0.3–0.8 mm), respectively. Embedded healing occurred more frequently in the reinserted implants than in the primary implants (p = 0.052). The patients’ satisfaction suffered from implant failure, but a successful reimplantation could reverse it with close doctor–patient communication. (4) Conclusions: Reimplantation treatment was recommended, based on a thorough evaluation and consideration of the risk factors combined with effective communication with the patients.