This paper presents a study on evaluating rolling shear (RS) strength properties of cross laminated timber (CLT) using torsional shear tests and bending tests. The CLT plates were manufactured with Spruce-Pine-Fir boards and glued with polyurethane adhesive. Two types of layups (3-layer and 5-layer) and two clamping pressures (0.1 MPa and 0.4 MPa) were studied. For the torsional shear tests, small shear block specimens were sampled from the CLT plates and the cross layers were processed to have an annular cross section. Strip specimens were simply sampled from the CLT plates for the bending tests. Based on the failure loads, RS strength properties were evaluated by torsional shear formula, composite beam formulae as well as detailed finite element models, respectively. It was found that the two different test methods yielded different average RS strength value for the same type of CLT specimens. The test results showed that the CLT specimens pressed with the higher clamping pressure had slightly higher average RS strength. The specimens with thinner cross layers also had higher RS strength than the specimens with thicker cross layers.