Among the possible solutions for achieving low friction, polymer brushes that are grafted onto surfaces are good candidates. The tribological characterization of such layers becomes more difficult when the friction is lower: the signal-to-noise ratio of the friction force that is measured with conventional tribometers impedes the precise quantification. Therefore, we have applied a new technique that has been developed at the Laboratory of Tribology and System Dynamics (LTDS), called the ‘oscillating relaxation tribometer’. The advantage of this original technique is that it characterizes low friction with unequalled sensitivity. The lower the friction, the better the precision, and it permits obtaining the ‘friction law’ directly from robust and rapid experimental tests. In this study, the samples that have been used are the ionic liquid-type polymer brushes (ILPBs) with different thicknesses, which have been grafted onto silicon wafers and steel coupons. The counter-face is a mirror-polished steel ball. We show that (i) a thick ILPB layer on silicon is very resistant to high contact pressure, up to 555 MPa; (ii) the friction behavior that is obtained is close to that of a Newtonian viscous one, even under maximum normal loads; (iii) poorer results are obtained for the thinner sample; and (iv) the repetition, up to 5000 oscillations on the same surface, does not affect the friction damping of the contact, which demonstrates that this film provides a favorable resistance to friction under severe contact conditions. In addition, the feasibility of grafting onto steel surfaces is demonstrated. The results are then discussed, with respect to friction and dissipation.