This article constitutes the first linguistic analysis of Maskilic Hebrew numerals. While it is commonly believed that Maskilic Hebrew exhibited a normative grammatical structure based largely on the biblical standard, examination of Maskilic texts reveals a much more diverse reality including elements of Biblical, Rabbinic, Medieval, and later Hebrew, as well as Yiddish and German, a reflection of the authors' rich linguistic background. The article explores the intriguing ways in which these different elements manifest themselves in Maskilic Hebrew numeral morphosyntax and usage. It analyses the key features of the numeral system drawing on examples from prominent Maskilic Hebrew texts of various fiction and nonfiction genres. These features include the avoidance of the dual in favor of the plural with the numeral 'two' (e.g., 'two years'); word order with basic and compound numerals (e.g., WW versus WW 'three days'; versus 'twenty five '); equalization of polar agreement (e.g., 'four princes' and 'six ships'); the use of the absolute and construct forms with numerals (e.g., WWV 'the five months'); the use of ordinals to indicate hours (e.g., 'at four o'clock); and the use of the German ordinal markers and to indicate dates (e.g., 20 'on the twentieth of September). The article provides a diachronic perspective on these Maskilic Hebrew features by examining their relationship with earlier forms of the language as well as with Modern Hebrew.