Due to compressive loads, offshore flexible pipes may exhibit global and local instabilities and as a consequence structural failures. This work presents an experimental investigation concerning the local structural behavior of a real 2.5-inch flexible pipe under compressive load. Three instabilities events were observed in the experimental test: elephant’s foot buckling, birdcaging and wrinkling. Digital image correlation techniques, applied for the first time in this scenario, allowed a clear experimental assessment. Correspondence between axial compressive loads and observed instabilities is discussed. Linear elasticity formulations are used to explain the structural behavior, culminating on an instability diagram for elephant’s foot buckling deflagration, based on a von Mises stress yielding criterion.