Majo no Jouken (1999)

Both are romances between a teacher/tutor and his or her student, but they are gender-flipped and in MNJ the leads are much closer in age than in TWYLTDM.

One is historical and the other modern, but both are a forbidden and complex love story between the older FL who is the teacher of the younger ML. Both MLs fall first, and both have an issue with their parent that causes many obstacles for the leads to be together. Both dramas have somewhat open endings that can be interpreted as happy or a dream.

The two dramas have many points in common: both are about the relationship between a male student and a female teacher. Their story is troubled due to social pressure.