Comb-like graft copolymers with carbohydrate side chains have been developed as aqueous lubricant additives for oxide-based tribosystems, in an attempt to mimic biological lubrication systems, whose surfaces are known to be covered with sugar-rich layers. As adopted in the previous studies of the graft copolymer poly(L-lysine)-graft-poly(ethylene glycol) (PLL-g-PEG), which showed both excellent lubricating and antifouling properties, a similar approach was chosen to graft dextran chains onto the same backbone, thus generating PLL-g-dex. PLL-g-dex copolymers readily adsorb from aqueous solution onto negatively charged oxide surfaces. Tribological characterization at the macroscopic scale, either under pure sliding conditions or a mixed sliding/rolling contact regime, shows that PLL-g-dex is very effective for the lubrication of oxide-based tribosystems. The relative lubricating capabilities of PLL-g-dex copolymers compared with PLL-g-PEG copolymers were observed to be highly dependent on the molecular structure of the copolymers (in particular, sidechain density along the backbone) and the measurement conditions (in particular, time between tribocontacts); the PLL-g-dex copolymers with a low degree of grafted side chains (B20% grafting of available protonated primary amine groups along the backbone) showed better lubricating performance than their PLL-g-PEG counterparts at high tribocontact frequency (Cca. 0.32 Hz).