This study aimed to examine the retentive characteristics of each retentive element material and the effects from thermocycling using the two implant-retained mandibular overdenture model. Two stud abutments and three retentive element materials; nylon, polyetheretherketone (PEEK) and polyvinylsiloxane (PVS) were used in this study. Four tested groups, with a total of 40 overdentures, were fabricated, including a Locator® abutment with nylon retention insert (NY), Novaloc® abutment with PEEK retention insert (PK), Locator® abutment with PVS retention insert (RL), and Novaloc® abutment with PVS retention insert (RN). The retentive force (N) was measured before thermocycling, and at 2500, 5000, and 10,000 cycles after thermocycling. Significant changes in the percentage of retention loss were found in the NY and PK groups (p < 0.05) at 6 and 12 months for the RL group (p < 0.05) after artificial aging. The RN group exhibited a constant retentive force (p > 0.05). The tendency of the percentage of retention loss significantly increased for PEEK, nylon, and PVS silicone over time. The results of the present study implied that retentive element materials tend to lose their retentive capability as a result of thermal undulation and water dispersion. Nylon and PEEK, comprising strong polar groups in polymer chains, showed a higher rate of retention loss than polyvinylsiloxane.