I explore the current ability of both white dwarf cooling theory and main-sequence stellar evolution theory to accurately determine stellar population ages by comparing ages derived using both techniques for open clusters ranging from 0.1 to 4 Gyr. I find good agreement between white dwarf and main-sequence evolutionary ages over the entire age range currently available for study. I also find that directly comparing main-sequence turnoff ages to white dwarf ages is only weakly sensitive to realistic levels of errors in cluster distance, metallicity, and reddening. Additional detailed comparisons between white dwarf and main-sequence ages have tremendous potential to refine and calibrate both of these important clocks, and I present new simulations of promising open cluster targets. The most demanding requirements for these white dwarf studies are very deep (V ≥ 25-28) cluster observations made necessary by the faintness of the oldest white dwarfs.