Cross-laminated timber (CLT) panels are fabricated with their layers stacked crosswise. Owing to the low shear modulus and strength in the rolling shear direction, the shear properties of cross-layers influence the overall deflection and shear capacities of CLT panels. The aim of the present study is to determine the rolling shear properties of Japanese cedar and investigate how annual ring patterns and lamina geometry influence shear properties. Using a test configuration similar to the standard shear test configuration prescribed in European Standards (EN 408), a single lamina shear test was conducted. To investigate the influence of thickness-to-width aspect ratio of the lamina on the rolling shear properties, samples with three different widths, including 62, 88, and 112 mm, with a constant thickness of 24 mm were tested. The geometrical features of the annual ring patterns of each test sample were measured. The mean rolling shear moduli were 72, 91, and 109 MPa, and the mean rolling shear strengths were 1.54, 1.83, and 2.02 MPa for the 62-, 88-, and 112-mm sample widths, respectively. Shear strength was highly correlated with shear modulus. The mean shear modulus and strength, in addition to the 5% quantile, increased with an increase in lamina width. Across all sample widths, rolling shear modulus and strength decreased with an increasing radial distance from the pith. Using the principle of continuum mechanics, the influence of the annual ring angle relative to the shear force direction was examined quantitatively using the finite element method. The results suggest that shear modulus and its variance are influenced greatly by the annual ring structure.