The paper deals with the grammatical semantics of iterative verbs like хаживал, бивал, etc., in Russian sources of the 15th—17th centuries and their subsequent evolution in Russian. The principal characteristic of such verbs is their inability to express processual meaning. In the 15th—17th centuries they were used mainly to express generalized factual past tense, as they are still used in modern North Russian dialects; the semantic basis of this meaning is discreteness of action and its potential recurrence. Although such verbs in context can also refer to a single action, potential reproduction of the situation is inherent in their semantics. The meanings of a habitual action in the past and of a remote action were contextually conditioned in the 15th—17th centuries, later (presumably by the end of the 18th century) in Central Russian dialects the semantics of such forms grew narrower and the notion of past habituality became grammaticalized.