There is no requirement for the ball to EVER enter the glove. The requirement is for the pitcher to bring the hands together, and to do this once and only once before delivering the ball.
Quote:
ASA Rule 6
Section 3. LEGAL DELIVERY.
A. The pitcher must not make any motion to pitch without immediately delivering the ball to the batter.
B. The pitcher must not use a pitching motion in which, after bringing the hands together, the pitcher removes one hand from the ball, and returns the ball to both hands.
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Your pitcher is likely violating both "A" and "B".