The paper presents direct measurement of in-cylinder friction from a single cylinder motocross race engine under motored conditions and compares the same with a new analytical predictive method. These conditions are encountered in piston-cylinder system with the application of cylinder deactivation (CDA) technology, which is a growing trend. The analytical method takes into account the various regions within instantaneous contact of compression ring-cylinder liner, including lubricant film rupture, cavitation zone and the subsequent lubricant film reformation. The analysis also includes the effect of boundary friction and lubricant rheology. The predictions and direct measurements of cyclic friction show good agreement and indicate dominance of viscous friction under the investigated engine running conditions. In particular, it is shown that the compression ring contribution to in-cycle friction is most pronounced in the region of high cylinder pressures because of combined Poiseuille friction and some boundary solid interactions. The combined experimental-analytical approach has not hitherto been reported in literature.