Many rocks contain planar heterogeneities, in the form of open fractures, veins and/or stylolites, but scarce data exist on how strength and fracture pattern formation is affected by the presence of a singular planar heterogeneity in an otherwise uniform matrix. The mechanics of stylolite-bearing and/or fractured limestone is of interest to several engineering applications, from quarries to subsurface gas or geothermal reservoirs. We have performed Brazilian Disc tests on pre-fractured Indiana limestone samples and Treuchtlinger Marmor discs which contain cohesive stylolites, investigating Brazilian test Strength and the resulting fracture pattern. All experiments were filmed, and where possible analyzed with particle image velocimetry. When viewed in 2D, the planar discontinuity was set at different rotation angles compared to the principal loading direction, where perpendicular to the loading direction is defined as 0⁰. The results show that all samples are weaker than their intact counterparts. For the pre-fractured Indiana limestone, there is 10–75% angle-dependent weakening. However, in the samples with a stylolite, strength is weakened by 35–75%, independent of direction. Several new cracks appeared when fracturing a stylolite-sample, where the orientation is heavily influenced by the stylolite orientation. The fracture pattern and associated stress drops are more complex for high angles. In these samples always more than one fracture formed, whereas in pre-fractured samples usually only one new fracture formed. This suggests a potential for more permeability increase when hydrofracturing a stylolite-rich interval. Comparison with Finite Element Models indicates that this difference in fracture pattern is caused by the strength contrast between the anastomosing stylolite zone and the matrix material, leading to stress concentrations effects. This causes (micro-) fracture nucleation to occur locally, promotes fracture coalescence and fracture growth at lower overall sample-load conditions compared to intact samples.