watershed has 10 distinct synonyms spread across 3 of its 3 senses. Each sense below keeps its own list, because a synonym belongs to a meaning and not to a word: swapping one sense's substitute into another sense's sentence is how a thesaurus makes writing worse. WordNet records no antonym for it — antonymy is a relation between word forms rather than concepts, so it is deliberately sparse.
Counts are distinct word forms across every sense. A synonym that appears under three senses is counted once here and shown three times below, under each sense it belongs to.
a ridge of land that separates two adjacent river systems
the entire geographical area drained by a river and its tributaries; an area characterized by all runoff being conveyed to the same outlet
“flood control in the Missouri basin”
an event marking a unique or important historical change of course or one on which important developments depend
“the agreement was a watershed in the history of both nations”
Synonyms, antonyms and the broader and narrower relations for watershed come from Princeton University’s WordNet. Full sources and licences.