The purpose of this study was to examine writing assessment according to raters’ career length and gender. A total of 83 teachers were asked to rate essays written by students following completion guidelines in an empathizing task. The results showed that writing assessments differed by teachers’ career length and by assessment criteria, and that assessments changed based on the gender of both the students and raters, thus revealing gender bias and same-sex depreciation. These outcomes suggest the following: First, teachers should control writing task criteria. Second, rater gender should be controlled in large-scale writing assessments. Lastly, teachers should examine and reflect on their own writing assessment skills even if they have sufficient teaching experience.