In recent years, cultural intelligence (CQ, or the ability that an expatriate has to adapt across cultures), cultural effectiveness (the ability to interact and communicate with host nationals), and cultural adjustment are regarded as three of the most important factors for expatriate performance. However, the interrelationships among these variables have largely been ignored. Moreover, the role of previous international experiences on the above interrelationships has also not been determined. This study focuses on how CQ and expatriates’ experience affects cultural adjustment, cultural effectiveness, and expatriates’ performance. Two-hundred and twenty-two expatriates of Taiwanese multinational companies (MNCs) participated in the survey. The findings indicate that personality and expatriate training have significant and positive effects on expatriates’ cultural intelligence and cultural adjustment. Moreover, the research results report that CQ has positive and significant effect on expatriate performance. Interestingly, the proposed model which is tested by using SEM indicates that there is no significant effect of CQ on cultural adjustment, even though the direction is positive. However, the regressions results indicate that CQ has positive and significant effects on cultural adjustment. The reason is since too many variables interact in the proposed model, thus, the results only show that CQ has direct influence on expatriate performance. Finally, this study reveals that previous international experiences could serve as moderating variables. Having more international experiences do not mean that expatriates will have higher level of expatriate performance, unless they also have higher cognitive CQ and motivational CQ. Surprisingly, when expatriates have lower level of cognitive CQ and motivational CQ, having more international work and travel experiences lead to lower level of performance. Interestingly, the level of expatriate performance is higher when the expatriates have less international experiences with higher CQ, compare to those expatriates having lower experiences and lower CQ. Managerial implications as well as future research directions are also presented.