In this study, the researcher aimed to develop a mobile-assisted learning system and to investigate whether it could promote teenage learners' classical Chinese learning through the flipped classroom approach. The researcher first proposed the structure of the Cross-device Mobile-Assisted Classical Chinese (CMACC) system according to the pilot survey and reviewed literature, and then adopted a quasi-experimental design to understand whether the developed system could promote and support flipped classroom learning for classical Chinese. A total of 56 eleventh graders from two classes participated in the experiment. The learners in the experimental group learned classical Chinese with the flipped classroom learning strategy with the assistance of the CMACC system, while the control group adopted the flipped classroom learning strategy without using the CMACC system. The results reveal that all of the students improved their Chinese performance, but it was noticeable that the learners who used the CMACC system showed better motivation in terms of self-directed preview learning, while those who only learned with the traditional textbooks tended to be more passive. In sum, the mobile-assisted learning system added value in providing learners with opportunities to achieve anytime and anywhere flipped classroom learning. The integration of ubiquitous mobile learning technology and the flipped classroom strategy can be viewed as a critical factor leading to students achieving self-regulated learning. It is also suggested that instructors should carefully take the targeted learners' cultural background and the availability of supporting learning devices into consideration so as to prevent the flipped classroom from exacerbating the digital divide. Other suggestions for educators and instructional designers are also proposed.