YOU SAID:

I like to watch my dog as he’s watching his own watch

INTO JAPANESE

私は自分の時計を見ている犬を見るのが好きです

BACK INTO ENGLISH

I like watching dogs looking at their watches.

INTO JAPANESE

犬が時計を見ているのを見るのが好きです。

BACK INTO ENGLISH

I like watching my dog look at the clock.

INTO JAPANESE

私の犬が時計を見るのを見るのが好きです。

BACK INTO ENGLISH

I like watching my dog look at the clock.