Being described as two sides of one coin, language and culture are increasingly recommended to be inseparably addressed. Thanks to technological advances, this is now more feasible than before. In response, this study examined the comparative effects of synchronous and asynchronous telecollaborative digital media projects (DMPs) on learners' macro- and micro-level oral proficiency and intercultural competence. Telecollaboration took place between Egyptian TEFL (Teaching English as a Foreign Language) student-teachers (N = 56, randomly selected) and a convenient sample of English natives (N = 28) at Michigan State University in the US. Each group was randomly assigned to two groups: synchronous and asynchronous. The concurrent triangulation mixed-method design was followed to collect and analyze both quantitative and qualitative data. The study concluded that synchronous and asynchronous telecollaborative DMPs yielded improvements in all micro- and macro-level oral proficiency skills except discourse management, which did not only improve among the synchronous participants but also retreated among the asynchronous ones. Also, synchronous telecollaborators outperformed the asynchronous ones in all macro- and micro-level skills except vocabulary and grammar. Besides, despite improvement after telecollaboration, none of the four groups outdid the others either in overall or factor-level intercultural competence. Qualitative findings revealed that TEFL participants appreciated telecollaboration and DMP generation and exchange activities, whereas they were dissatisfied with the inadequate and unequal opportunities for interaction with the natives, native speakers being too natural, and being restricted to single-mode interaction. However, they reported a number of linguistic, cultural, and emotional gains from these experiences.