A new class of bifunctional hydrogen‐bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen‐bond donor distances is reported. Oxoporphyrinogens are highly non‐planar rigid macrocycles containing a multiple hydrogen bond‐forming binding site. In this work, we describe the first example of non‐planar OxPs as hydrogen‐bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β‐substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4‐conjugate additions and sulfa‐Michael additions, as well as, Henry and aza‐Henry reactions at low catalyst loadings (≤ 1 mol‐%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi‐functional activation of both substrates through hydrogen‐bonding interactions.