Motivation constitutes one of the language teachers’ main affective factors that tends to exert considerable influence on their pedagogical efficacy and is likely to determine their resilience in various language contexts and academic settings. The present study scrutinized the main factors in Italian and Iranian English teachers’ motivation. Furthermore, it examined the difference between the motivation of these teacher groups. Using convenience sampling, the study gathered data from 281 Italian and 231 Iranian English educators. The participants completed six validated assessment instruments designed to measure teacher motivation, teaching enjoyment, teacher reflection, psychological well-being at work, emotion regulation, and work engagement. Lastly, they analyzed the obtained data using multiple-regression test and a t-test. The results of the study indicated that Italian teachers’ teaching enjoyment, work engagement, and teacher reflection were the main factors in their motivation. On the other hand, Iranian teachers’ psychological well-being at work, emotion regulation, and work engagement were the significant predictors of their motivation. Furthermore, Italian teachers’ motivation was significantly higher than that of Iranian teachers. The results of the study are likely to provide guidelines on the development of education courses and manuals for English teachers in foreign language contexts.