Single-implant overdentures (SIOs) represent a major biomechanical challenge in terms of prosthetic retention. The Novaloc attachment system has the potential to overcome those challenges when used for SIOs, due to the use of PEEK matrices. This study compared the retentive force of the Novaloc attachment to the traditional Locator system, before and after cyclic insertion–removal cycles. Three Novaloc matrices (white, yellow, and green, corresponding to low, medium, and high retention, respectively) and Locator (medium retention) were tested, totalling four groups. Retentive force was measured using an Imada force gauge before and after 1095 insertion–removal cycles, corresponding to a year of SIO wearing. Retention was tested with the implants angulated at 0, 10, and 20°. Data for the different groups, angles, and cycling periods were tested via linear regression analysis and two-way ANOVA (α = 0.05). Although the Locator system yielded higher retention forces in general, it lost a much higher percentage of retention with cycling. This trend was similar with the three angles, with forces being inversely proportional to the implant angulation. The authors conclude that Novaloc may provide more reliable retention for SIOs due to their higher resistance to insertion–removal cycling.