We construct nontrivial L-equivalence between curves of genus one and degree five, and between elliptic surfaces of multisection index five. These results give the first examples of L-equivalence for curves (necessarily over non-algebraically closed fields) and provide a new bit of evidence for the conjectural relationship between L-equivalence and derived equivalence. The proof of the L-equivalence for curves is based on Kuznetsovs Homological Projective Duality for Gr(2,5), and L-equivalence is extended from genus one curves to elliptic surfaces using the Ogg--Shafarevich theory of twisting for elliptic surfaces. Finally, we apply our results to K3 surfaces and investigate when the two elliptic L-equivalent K3 surfaces we construct are isomorphic, using Neron--Severi lattices, moduli spaces of sheaves and derived equivalence. The most interesting case is that of elliptic K3 surfaces of polarization degree ten and multisection index five, where the resulting L-equivalence is new.