To enhance the five-axis machine-tool performance, it is significant to avoid the singular configuration where the kinematic and dynamic performances degrade dramatically. Most existing methods aim at solving this issue by avoiding the singularity posture in the geometric manner. Different from them, this paper aims at avoiding the singular phenomenon by reducing the Jacobian-matrix condition number, and proposes an adaptive singularity avoidance toolpath generation method. This method adds a damping diagonal matrix into the computation of the pseudo-inverse Jacobian matrix to reduce its ill-condition extent during axial path generation, thus solving the singularity phenomenon. However, the adding of damping matrix gives arise to the toolpath error. To ensure the accuracy meanwhile, an adaptive law for determination of the damping matrix is presented to balance the singularity-avoiding effect and the path error, under the constraints of condition number and tool-orientation error-tolerance thresholds, as well as invariant cutter-contact points. Simulation and experimental tests verify that the proposed method can not only realize the singular avoidance without preliminary adjustment of the original toolpath, thus can be realized in real-time NC system, but also has better singular-avoiding performance and lower toolpath error when comparing with typical methods.