In existing wood strength prediction models for parallel to grain failure in timber connections using dowel-type fasteners, different methods consider the minimum, maximum, or summation of the tensile and shear capacities of the failed wood block planes. It is postulated that these methods are not appropriate since the stiffness of the adjacent wood loading the tensile and shear planes differs, and this leads to uneven load distribution among the resisting planes. A closed-form analytical method to determine the load-carrying capacity of wood under parallel-to-grain loading in small-dowel-type connections in timber products is thus proposed. For the wood strength, the stiffness of the adjacent loading volumes and strength of the failure planes subjected to nonuniform shear and tension stresses are considered. The effective wood thickness for the brittle failure mode is derived and related to the elastic deformation of the fastener. A mixed failure mode is also defined (a mixture of brittle and ductile) and depends on the governing ductile failure mode of the fastener. To help the designer, an algorithm is presented that allows the designer to calculate the resistances associated with predictions of the different possible brittle, ductile, and mixed failure modes. The proposed stiffness-based model has already been verified in brittle and mixed failure modes of timber rivet connections. In the research reported in this paper, an extended application is proposed for other small-dowel-type fasteners such as nails and screws. Results of nailed joint tests on laminated veneer lumber (LVL) and the test data available from the literature on glulam confirm the validity of this new method, and show that it can be used as a design provision for wood load-carrying capacity prediction of small-dowel-type timber connections.