Abu Labid (may Allah have mercy on him) said: One day al-Hakam bin Ayyub (may Allah have mercy on him) sent out horses (for a race). We said: "If we go to Sayyiduna Anas bin Malik (may Allah be pleased with him), we will ask him." We asked Sayyiduna Anas bin Malik (may Allah be pleased with him): "Did you use to wager on horse races in the time of the Prophet (peace and blessings be upon him)?" He said: "Yes; indeed, the Prophet (peace and blessings be upon him) wagered on a horse that was called Subhah. That horse won the wager, and he (peace and blessings be upon him) was delighted by it and was pleased with it."
Hadith Referenceالسنن الكبرى للبيهقي / كتاب السبق والرمي / 19774
Musa bin Ubayd (may Allah have mercy on him) said: After praying the dawn prayer we stayed in the Hijr until morning. When it had become fully light, we saw that Abdullah bin Umar (may Allah be pleased with them both) was also there. He was asking each man one by one: "Where did you pray the morning prayer?" He was asking everyone, until he asked me: "O Ibn Ubayd, where did you pray?" I said: "Here." He was pleased and said: "We do not know of any prayer of greater virtue than praying the morning prayer in congregation on Friday." They asked him: "O Abu Abd al-Rahman, did you use to wager on horse races in the time of the Prophet (peace and blessings be upon him)?" He said: "Yes; indeed, the Prophet (peace and blessings be upon him) wagered on a horse, and he (peace and blessings be upon him) won."
The Shaykh (may Allah have mercy on him) said: This, if it is authentic, means only that one of the two horsemen raced his companion with the stake coming from him alone, not from his companion. And Allah knows best.
Hadith Referenceالسنن الكبرى للبيهقي / كتاب السبق والرمي / 19775
Sayyiduna Iyad al-Ash'ari (may Allah be pleased with him) said: Sayyiduna Abu Ubaydah (may Allah be pleased with him) said: "Who will wager with me?" A young man said: "I will, if you will not be angry." The narrator said: So the young man outran him. I saw the two braids of Sayyiduna Abu Ubaydah (may Allah be pleased with him) bouncing, while he was behind him on an Arab horse.
Hadith Referenceالسنن الكبرى للبيهقي / كتاب السبق والرمي / 19776
Sayyiduna Abdullah bin Mas'ud (may Allah be pleased with him) narrates from the Prophet (peace and blessings be upon him) that he said: "Horses are of three kinds: one for the Most Merciful, one for Satan and one for man. The horse that is for the Most Merciful is the one a person ties up in the path of Allah; its urine and dung will be placed in his scale. The horse that belongs to Satan is the one on which wagers are made. The horse of man is the one by which he seeks his livelihood out of fear of poverty." If this is established, then, and Allah knows best, what is meant is that two people put up stakes and do not bring in a third between them, in which case it is not permissible.
Hadith Referenceالسنن الكبرى للبيهقي / كتاب السبق والرمي / 19777