Remember that time when a pair of shoes went missing at school?
Do you remember that incident when my (somebody's) shoes disappeared at school?
ご質問ありがとうございます。
① "Remember that time when a pair of shoes went missing at school?"＝「学校で靴が無くなったときのことを覚えている？」
② "Do you remember that incident when my (somebody's) shoes disappeared at school?"＝「学校で私の（誰かの）靴が消えた事件を覚えている？」
ご参考までに。
There was that incident at school where shoes disappeared wasn't there?
学校で靴がなくなる事件あったよね。
- There was that incident at school where shoes disappeared wasn't there?
- Back in middle school didn't students' shoes keep disappearing?
- Wasn't there an incident concerning shoes disappearing back when we were in middle school?
- Do you remember how shoes were disappearing at school?
Do you remember when 〇〇 lost his shoes back in junior high school?
Do you remember when someone took 〇〇's shoes when we were in middle school?
この場合、次のような言い方をすると自然で良いと思います。
ーDo you remember when 〇〇 lost his shoes back in junior high school?
「中学で〇〇くんが靴をなくしたときのこと覚えてる？」
ーDo you remember when someone took 〇〇's shoes when we were in middle school?
「中学で誰かが〇〇ちゃんの靴を取った時のこと覚えてる？」
Do you remember when ....?「…があったよね（覚えてる）？」を使って言うと良いですよ。
ご参考まで！
アメリカ合衆国 
カナダ 
