It is not possible. include/import statements operate with task files as a whole.
So with loops you'll have:
Task 1 with Item 1
Task 2 with Item 1
Task 3 with Item 1
Task 1 with Item 2
Task 2 with Item 2
Task 3 with Item 2
Task 1 with Item 3
Task 2 with Item 3
Task 3 with Item 3