Teacher emotions could make a difference to the development of technological pedagogical content knowledge (TPACK), a complicated knowledge essential for effective teaching with technology. Both experienced and novice teachers reported having experienced a series of emotional challenges as they acquire technology integration skills. Self-regulated learning (SRL), a series of cognitive and metacognitive learning processes in problem-solving, is associated with learners' emotions as well. In this paper, we examine the influence of teaching experience and SRL on teachers' emotions in the context of TPACK development. Particularly, we identify two distinct groups of teachers based on the extent to which they experience positive and negative emotional experience in the task using the clustering analysis method. Binary logistic regression was applied to test whether the model of teaching experience and SRL can predict previous emotion groups. Although the overall model was significant, only SRL was a significant individual predictor in this context. Regression analysis revealed a positive association between SRL and teacher emotions. We used a qualitative method to analyze teachers' think-aloud protocols to further determine teaching experience and SRL's influence on teacher emotions. The results supported previous findings that SRL can positively predict teachers' emotions during the TPACK development task. Implications were discussed for providing emotional support to teachers during TPACK development.