A two-dimensional Laser Induced Fluorescence (LIF) system was developed to visualize the oil distribution and study the oil transport in the piston ring pack of a single-cylinder diesel engine through an optical window on the liner. The system gives high spatial and intensity resolutions so that detailed oil distribution on the piston as well as between the rings and the liner can be studied. This work primarily focused on investigating different oil transport mechanisms on piston crown land and second land under various engine operating conditions. Oil accumulation on the crown land was observed under certain operating conditions and top ring up-scraping was deemed to be the source for this oil accumulation. Two mechanisms for the oil flow on the second land were identified, namely, inertia driven oil flow in the axial direction and oil dragging by gas flow in the circumferential direction. Finally, the effects of ring rotation were investigated.