Lip seals are components subjected to high mechanical stress and they are responsible for many out-of-service in pneumatic cylinders. The aim of this work is the development of an experimental methodology to evaluate lifetime duration and analyse failures and damages of rod lip seals for pneumatic cylinders. A dedicated test bench was designed and manufactured which reproduces actual working conditions of the seals i.e., compressed air action (seal pressurisation) and relative linear reciprocating motion. Three types of seals made of two elastomers (NBR and polyurethane) were tested; dry condition was considered to speed up the tests. The influence of geometric parameters like seal seat dimension and seal axis misalignment with respect to the rod axis, was analysed by multiple experimental tests. Results in terms of seal life duration and failure modes are presented which allow comparison of seals performance and provide a helpful tool to end-users in a proper selection of seals geometry, material and key working parameters.