Drilling systems and methods for enlarging a borehole that include an expandable reamer and an expandable stabilizer axially coupled above the expandable reamer are disclosed. The expandable reamer includes a tubular body having a longitudinal axis and a drilling fluid flow path therethrough, a plurality of generally radially and longitudinally extending blades carried by the tubular body, and a cutting structure carried by at least one blade of the plurality of blades, wherein at least one blade of the plurality of blades is movable outwardly with respect to the longitudinal axis. The expandable stabilizer includes a tubular body having a longitudinal axis and a drilling fluid flow path therethrough, a plurality of generally radially and longitudinally extending bearing pads carried by the tubular body, wherein at least one bearing pad of the plurality of bearing pads includes an up-hole cutting structure carried thereupon and is movable outwardly with respect to the longitudinal axis.