The repeated return of tetrapods to aquatic life provides some of the best-known examples of convergent evolution. One comparison that has received relatively little focus is that of mosasaurids (a group of Late Cretaceous squamates) and archaic cetaceans (the ancestors of modern whales and dolphins), both of which show high levels of craniodental disparity, similar initial trends in locomotory evolution, and global distributions. Here we investigate convergence in skull ecomorphology during the initial aquatic radiations of these groups. A series of functionally informative ratios were calculated from 38 species, with ordination techniques used to reconstruct patterns of functional ecomorphospace occupation. The earliest fully aquatic members of each clade occupied different regions of ecomorphospace, with basilosaurids and early russellosaurines exhibiting marked differences in cranial functional morphology. Subsequent ecomorphological trajectories notably diverge: mosasaurids radiated across ecomorphospace with no clear pattern and numerous reversals, whereas cetaceans notably evolved toward shallower, more elongated snouts, perhaps as an adaptation for capturing smaller prey. Incomplete convergence between the two groups is present among megapredatory and longirostrine forms, suggesting stronger selection on cranial function in these two ecomorphologies. Our study highlights both the similarities and divergences in craniodental evolutionary trajectories between archaic cetaceans and mosasaurids, with convergences transcending their deeply divergent phylogenetic affinities.