The fracture toughness in opening mode GIc for selected oil paints from Mecklenburg's Paint Reference Collection after approximately 30 years of natural ageing was determined using the procedure adopted from the ASTM D5528–13 standard in which double cantilever beam specimens are split in tensile tests. The careful reglueing procedure allowed multiple fracturing tests to be carried out that not only improved statistics of the measurements but also provided insight into the variation of the fracture toughness across the paint film observed for some paints. The latter was due to pigment sedimentation or chemical change of the oil binder as a result of the easier access of oxygen from the side open to the air. For the lead white paint, used over centuries both in paint films and oil grounds, the GIc values more than doubled from 18 to 39 J/m2 for three consecutive cracks formed at an increasing distance from one side of the paint film. The study demonstrated that fracture toughness corresponding to the first crack formation in aged oil paints ranged between 10 and 40 J/m2, relatively low values compared to the animal glue-based ground in paintings. In consequence, oil paints are more vulnerable to crack initiation and growth induced by tensile stress than the ground layer. The measurements filled the gap in the knowledge required for the analysis of fracturing or delamination processes in paintings.