This in vitro study aimed to evaluate the additive manufacturing (AM) of cobalt chromium Co-Cr and titanium Ti alloy clasps for clinical use. After scanning the Ni-Cr die of the first molar, Akers' clasps were designed using computer-aided design/ computer-aided manufacturing (CAD/CAM). The clasps were manufactured from Co-Cr-W dental alloy and Ti-6Al-4V alloy powder using AM machines. Then, they were divided into two groups. The initial retentive force of the clasps was measured using a universal testing machine. Cyclic loading of the clasps was carried out by a specially designed insertion-removal testing apparatus in wet condition up to 5000 cycles. Retentive force was measured at 1000, 2000, 3000, 4000, and 5000 cycles. Moreover, the intaglio surface of each clasp was scanned using the scanner; and superimposition between the pre- and post-cycling clasp files was performed to evaluate deformation after cyclic loading. The fitting surfaces of retentive clasp tips were examined with a scanning electron microscope (SEM). Finally, it has been found that the initial retentive force for the Co-Cr group was 10.81 ± 0.37 N, and for the Ti group was 5.41 ± 0.18 N. Additionally, during the testing periods, both Co-Cr and Ti clasps continued to lose retentive force within the cycles of placement and removal. This effect was more prominent in the Co-Cr than in the Ti clasps. The distances between pre- and post-cycling in the retentive arm were −0.290 ± 0.11 mm and −0.004 ± 0.01 mm in Co-Cr and Ti alloys, respectively, and in the reciprocal arm were −0.072 ± 0.04 mm and −0.032 ± 0.04 mm in Co-Cr and Ti alloys, respectively. The retentive force required to remove the Ti clasps was found to be significantly lower than those required to dislodge the Co-Cr clasps. Co-Cr and Ti clasps lost significant amounts of retentive force from the initial use to the 3.5-year periods of simulated clinical use.