1)
When did Daniel see this?
1.
Rashi: In his first dream that he told above.
2)
With which Kadishin did it make war?
1.
Rashi: With Yisrael. Ibn Ezra (18) ? the last king of Yishmael will do great evil to Yisrael. He will want to change Yisrael's Mo'adim and Torah. Yisrael will be in great affliction until "Idan v'Idanin u'Flag Idan" (7:25).
2.
Malbim: In olden days, [Romi] fought against Yisrael's creed, via debates and decrees to make them abandon their creed, and succeeded.
