The Old Trafford boss was taking part in the charity auction when a particular juicy lot presented itself - a round of golf with former Manchester United striker Dwight Yorke.
However, he faced competition for the prize from his assistant Ryan Giggs.
In jest, and to much laughter from the audience at the awards evening - including from Yorke who was sat behind, Van Gaal clipped Giggs around the ear for daring to compete with him.
With Van Gaal appearing to enjoy himself, he went on to deliver a rambling speech before storming back onto the stage to demand the audience applaud a female saxophonist.
Caption competition
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