Relative pronoun 'when' and 'where'

Hi teachers!

Please check the sentences below and let me know which are not grammatical. I especially wonder about # 4 5, 9 and 10.

1. I remember the day when he left me. (0)

2. I remember the day on which he left me. (0)

3. I remember the day which he left me on. (0)

4. I remember the day that he left me on. (?)

5. I remember the day that he left me. (?)

6. This is the city where I was born. (0)

7. This is the city in which I was born. (0)

8. This is the city which I was born in. (0)

9. This is the city that I was born in. (?)

10. This is the city that I was born. (?)

So many thanks ??