I assume that by “anticlockwise” you mean “with the same verse of rotation by which the positive $x$-semiaxis reaches the positive $y$-axis by the least angle”; “clockwise” is the opposite verse of rotation.
Then multiplication by $-i$ induces a clockwise rotation by a right angle, because $1\cdot(-i)=-i$, which in the standard representation of complex numbers has a negative $y$-coordinate.
As you see, there are many implicit assumptions in the statement of the problem.
If you decide to represent the $x$-axis in the usual fashion (horizontal, positive verse from left to right) and the $y$-axis upside down with respect to the usual way, then, with the intuitive understanding of clockwise and anticlockwise, multiplication by $-i$ induces an anticlockwise rotation by a right angle. That's why I initially gave a definition that's independent on the graphical representation.
Another case: suppose your teacher is drawing on a side of a transparent board and you're on the opposite side; you and the teacher will see different verses of rotation, under the common understanding of clockwise ad anticlockwise. Not if you stick to the definition I gave.
By the way, the “anticlockwise” verse I defined at the top is usually and better called positive.