One of the major prerequisites for calculating piston ring friction is a good description of the tribological situation. A very important condition for describing the frictional behavior of a piston ring correctly is knowledge about the amount of lubricant present. For piston rings the external load may be established by measuring the pressure distribution, i.e. the pressure drop in the piston ring package. Speed and temperature may also be established. The amount and distribution of oil present is, however, not easily determined. It is often assumed that it operates under fully flooded conditions, but this is not the case in real life operation. These problems forms the basis for the experimental investigation. In large two-stroke engines the cylinder oil is supplied to the bearing at discrete locations on the cylinder liner at a specific rate at a certain time. The shifting in lubrication regimes and the non-uniform oil distribution opens for the possibility of starved conditions for the piston ring bearing. Therefore it is important to measure the oil distribution on the liner as a function of the operating conditions. The amount of lubricant available is reflected in the friction absorbed in the bearing. Since the frictional forces are small compared to the rest of the acting forces the rig is designed such that the piston is fixed while the cylinder liner moves. This approach makes it simple to measure the parameters mentioned above by putting the instrumentation in the piston assembly. The aim of this paper is to investigate the tribological condition between a piston ring and cylinder. A test apparatus is used to study the interaction between a piston ring and a cylinder liner. In large two stroke engines with cross head bearings the piston height is small compared to smaller four stroke engines where the skirt transfers the guide forces to the cylinder liner. The power loss due to piston skirt friction is estimated by comparing two different piston designs. The piston ring experiences hydrodynamic, mixed and boundary lubrication and the squeeze effect of the piston ring is significant. Experimental results are presented and the influence from speed, number of piston rings, lubrication oil type and supply oil is discussed.