Recent trend of research indicates that not only massive but also massless (asymptotic Newtonian mass zero) wormholes can reproduce post-merger initial ring-down gravitational waves characteristic of black hole horizon. In the massless case, it is the non-zero charge of other fields, equivalent to what we call here the "Wheelerian mass", that is responsible for mimicking ring-down quasi-normal modes... In this paper, we enquire whether the same Wheelerian mass can reproduce black hole observables also in an altogether different experiment, viz., the strong field lensing. We examine two classes of massless wormholes, one in the Einstein-Maxwell-Dilaton (EMD) theory and the other in the Einstein-Minimally-coupled-Scalar field (EMS) theory. The observables such as the radius of the shadow, image separation and magnification of the corresponding Wheelerian masses are compared with those of a black hole (idealized SgrA* chosen for illustration) assuming that the three types of lenses share the same minimum impact parameter and distance from the observer. It turns out that, while the massless EMS\ wormholes can closely mimic the black hole in terms of strong field lensing observables, the EMD wormholes show considerable differences due to the presence of dilatonic charge. The conclusion is that masslessless alone is enough to closely mimic Schwarzschild black hole strong lensing observables in the EMS theory but not in the other, where extra parameters also influence those observables. The motion of timelike particles is briefly discussed for completeness. (read more)