Repeated bending over sheaves is one of the main causes of failure of synthetic fibre ropes used in marine operations. There are few published results available and even fewer models allowing lifetime to be estimated. A large new set of data from cyclic bend over sheave (CBOS) tests on 250 kN break load braided HMPE synthetic ropes is presented first, both tests to failure and interrupted tests followed by residual strength measurements. These data are analysed in order to propose an empirical lifetime model. This is identified using constant load tests, then evaluated for variable load sequences. A methodology to include rope lifetime prediction in handling system design is then discussed.