A silver-catalyzed trans addition of carboxylic acids to ynol ethers is described. The reaction has a broad scope with respect to carboxylic acids and ynol ethers, delivering (Z)-α-alkoxy enol esters in good yields with excellent regio- and stereoselectivity. Meaningfully, the Ni-catalyzed selective coupling of alkenyl C-OPiv bonds of (Z)-α-alkoxy enol esters with boronic acids enables a convenient route to the access of (E)-enol ethers. As such, the two-step procedure, consisted of a hydrocarboxylation and a subsequent Suzuki-Miyaura coupling, offers a formal trans hydroarylation of ynol ethers, thus providing a good complementary method to our previous report.