The use of cross-laminated timber (CLT) in multi-story buildings is increasing due to the potential of wood to reduce green house gas emissions and the high load-bearing capacity of CLT. Compression perpendicular to the grain (CPG) in CLT is an important design aspect, especially in multi-storied platform-type CLT buildings, where CPG stress develops in CLT floors due to loads from the roof or from upper floors. Here, CPG of CLT wall-to-floor connections are studied by means of finite element modeling with elasto-plastic material behavior based on a previously validated Quadratic multi-surface (QMS) failure criterion. Model predictions were first compared with experiments on CLT connections, before the model was used in a parameter study, to investigate the influence of wall and floor thicknesses, the annual ring pattern of the boards and the number of layers in the CLT elements. The finite element model agreed well with experimental findings. Connection stiffness was overestimated, while the strength was only slightly underestimated. The parameter study revealed that the wall thickness effect on the stiffness and strength of the connection was strongest for the practically most relevant wall thicknesses between 80 and about 160 mm. It also showed that an increasing floor thickness leads to higher stiffness and strength, due to the load dispersion effect. The increase was found to be stronger for smaller wall thicknesses. The influence of the annual ring orientation, or the pith location, was assessed as well and showed that boards cut closer to the pith yielded lower stiffness and strength. The findings of the parameter study were fitted with regression equations. Finally, a dimensionless ratio of the wall-to-floor thickness was used for deriving regression equations for stiffness and strength, as well as for load and stiffness increase factors, which could be used for the engineering design of CLT connections.