This study examines the flexural performance of six 9-m full-scale two-span Nail-Laminated Timber Concrete (NLTC) composite slabs. The slabs were made with lumber beams edge-joined with double nailing, end-joined with butt joints, and the reinforced concrete topping connected with a set of notches, inclined screws, or a combination of both. The multi-span configuration of slabs reduces their deflections simply and effectively. Five-point monotonic bending tests were considered for all slabs. Before full-scale slabs, compressive and tensile pull-out tests of Timber-Concrete Composite (TCC) shear connections were performed, including notches and inclined screws. Tensile pull-out tests of shear connections were also included to emulate the negative bending moments that occur in the middle of the slabs. Failure modes, load–mid-span deflection relation, bending stiffness, and timber-concrete slip were evaluated for all slabs. A detailed 3D micro-Finite Element (FE) model of the shear connections was built in ANSYS software, whereas a macro-FE model of NLTC slabs was made in SAP2000, demonstrating a good fit for the timber-concrete interaction and the load-carrying capacity of the composite slab at the serviceability range. Moreover, an analytical elastic TCC beam with the Girhammar method was assessed and demonstrated as more precise than the traditional γ-method. Finally, an accurate prediction of the numerical and analytical (Girhammar) models for the bending stiffness at service loads up to 30% of capacity is observed, with errors in a range of 2–23% and 9–74%, respectively.