This study was to compare the shear bond strength (SBS) of different adhesives between metal orthodontic brackets on tooth surfaces and on tooth surfaces with amalgam restorations. Two hundred and fifty human upper premolars extracted for orthodontic purposes were randomly divided into two major groups; a tooth surface group and a 50% buccal amalgam restoration group. Brackets were bonded to the teeth using five different adhesives in each groups: I: UniteTM; II: Rely-a-bond®; III: Enlight®; IV: Transbond XTTM; V: Transbond PlusTM with self-etching adhesive. The teeth were thermocycled between 5° and 55° for 500 cycles, and consequently debonded using Instron testing machine to test the SBS. The enamel surfaces were examined under a stereomicroscope at 25X magnification and the amount of residual adhesive remaining on the teeth was determined with Adhesive Remnant Index (ARI) scores. The SBS values of all adhesives used on tooth surfaces were greater than the bonds of brackets on tooth surfaces with the amalgam restorations (p<.05). Significant differences among different adhesives did not exist in the tooth surface group (p>.05), but did exist in the amalgam restoration group (p<.05), in which Transbond XT and Enlight SBS values were significantly higher than Unite, Transbond Plus and Rely-a-Bond. In conclusion, the SBS values on tooth surfaces of all adhesives in this study were clinically acceptable (5.9-7.8 MPa)while three-step light-cured adhesives (Transbond XT and Enlight) had clinically acceptable SBS values on tooth surfaces with amalgam restorations.