Mhmwd bin Khalid محمود بن خالد · Jihad (Kitab Al-Jihad)

The Prophet (ﷺ) said: If one enters a horse with two others when he is not certain that it cannot be beaten, it is not gambling; but when one enters a horse with two others when he is certain it cannot be beaten, it is gambling.

The Messenger of Allah (ﷺ) used to give a quarter of the booty as reward after the fifty had been kept off, and a third after the fifth had been kept off when he returned.