This paper presents the results of an extensive series of direct shear tests covering a broad spectrum of bedding plane inclination angles with respect to the shearing plane to study the outcome of inherent anisotropy on the mechanical behavior of sand-steel interfaces. As a part of the research, it is shown that the peak friction and the maximum dilation angles of the tested inherently anisotropic sand are highly influenced by the bedding plane inclination angle. However, for smooth, intermediate, rough, and very rough sand-steel interfaces, the test results indicate that the variation in peak friction angle with the bedding plane inclination angle is meaningfully less than that for the same sand. Moreover, it is observed that the extrema of peak friction and maximum dilation angles in sand-steel interface tests are attained at bedding plane inclination angles that are significantly different from those obtained from direct shear tests on sand samples.