Modular floor slabs must be subdivided into prefabricable, transportable segments. This slab segmentation process conventionally uses a rectangular pattern, particularly for timber buildings. Regular segmentation patterns and strict column grids are ideal for rectangular building shapes, but restrict timber buildings to only some architectural uses, and are unideal for urban infill. Unfortunately, planning and constructing multi-storey wood buildings without a strict grid is still challenging. There is therefore a conflict between the desired column placement and the constraints imposed by building systems. This article investigates novel methods for segmenting timber floors supported by irregular column layouts. It proposes six different segmentation methods that are informed through Co-Design by structural, material waste, and transportation requirements. Co-Design allows for the direct integration and automated feedback of such diverse criteria into the early building design phase. These methods are based on three well-known computational approaches: Single-Objective Optimisation, Parametric Modelling, and Agent-Based Modelling. They could also be applied to other non-timber prefabricated floor systems. The segmentation methods are demonstrated on two example floor slabs with irregular column layouts, one with a rectilinear and the other with an irregular outline. The methods are compared using quantitative proxies for cost, fabrication time, architectural adaptability, and assembly complexity. More benchmark testing is needed, but initial results showed that the most efficient segmentations cannot adapt to irregular layouts, emphasising the need for a more adaptable approach to modular timber construction.