Nowadays, the use of timber as a building material is gaining more prominence. When designing timber structures, it is necessary to pay increased attention to the design of their connections. The commonly used connections are dowel-type connections, which are often used in combination with steel plates slotted into cut-outs in timber members. The presented paper deals with the behavior of double-shear bolted connections of squared timber and round timber with slotted-in steel plates. Several variants of connections with different distances between the fastener and the loaded end were selected for the experimental testing. A total of six types of test specimens were made from spruce timber, for which their selected physical properties were determined and evaluated before the experimental testing. Test specimens of bolted connections were first tested in tension parallel to the grain until failure under quasi-static loading. The connections were broken by splitting. Ductile failure preceded brittle failure. The actual load-carrying capacities were lowest for the lowest end distance. The load-carrying capacities for the middle and the longest end distances were comparable. The results of the experiments were then used for comparison with calculation procedures according to the standard for the design of timber structures and with calculations according to the theory of linear elastic fracture mechanics. The experiments and the analytical models were supported by a simple numerical analysis based on the finite element method.