This article addresses an important gap in existing scholarship on the history of teaching English as a foreign language (EFLT) in Italy. Increasing popularity of English in nineteenth-century Italy stimulated the production of a vast range of didactic materials, addressed specifically to Italian learners. In addition to new grammars, dictionaries and reading books, in the same period also letter-writing guides for learners of English started to circulate widely. Two such guides, Millhouse – Anderson (1873 [1856]) and Cann (1878) will be examined in this study. Fifty-five commercial model letters from each guide will be analysed, in order to investigate practices of teaching business English to nineteenth-century Italian learners. The study shows that translation, in the form of explanatory notes or glosses provided in Italian, was employed as the main teaching method in both guides, while comparison of the choices the two authors made as to what they decided to translate and how they translated these items indicates that they had divergent views on what specific linguistic features characterised the nineteenth-century commercial style of writing in English.