This study aimed to give a glimpse of the relationship of Teachers’ Humor Orientation (HO) and Style Utilization to Students’ Academic Performance in the Philippine Educational setting. A quantitative descriptive correlation design was employed through the use of the Humor Orientation Scale, Humor Style Checklist, and a Two-Phased Analysis of humor samples. The findings revealed that teachers had low HO levels and low variation in humor type utilization, surprisingly; students had outstanding grades in English. The test of relation showed no significant relationship between the variables. The study found out that its inability to identify effects of teachers’ HO level and Humor types to specific learning behavior (e.g., information acquisition, recall, retention) led a negative link to students’ outstanding academic performance. Further, the academic performance, as presented through grades, is too broad to correlate with any of the variables. However, the cross-referencing of qualitative results lead to some inconsistencies on the accuracy of the data which was based on self-report. Therefore, the study suggested moving one step backward and conducting experimental methods in the correlation of HO level and humor types to specific behaviors to provide evidence of correlation to students’ learning. Also, finding other methods would be a great future endeavor in the study of humor in the Philippine educational setting.