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What the Fathers say
Eastern Fathers
John Chrysostom
That He prays for this a second and a third time, comes of the feelings belonging to human frailty, through which also He feared death, thus giving assurance that He was truly made man. For in Scripture when any thing is repeated a second and third time, that is the greatest proof of its truth and reality; as, for example, when Joseph says to Pharaoh, And for that thou sawedst it twice, it is proof of the thing being established by God. (Gen. 41:32.)
Theophylact of Ohrid
He went away again the second time, and prayed, saying, O My Father, if this cup can not pass away from Me, except I drink it, Thy will be done. And He came and found them asleep again: for their eyes were heavy. And He left them, and went away again, and prayed the third time, saying the same words. When you hear that the Lord Himself prayed many times, learn, O man, that you ought to pray continuously when beset by temptations. When Jesus found them sleeping again, He did not rebuke them lest He grieve them, but He let them be. …
Western Saints
Jerome
Again, for the second time, he went away and prayed, saying: Father, if this chalice cannot pass away, unless I drink it, let your will be done. He prays for the second time, that if Nineveh cannot be saved in any other way, unless the gourd withers, let the will of the Father be done, which is not contrary to the will of the Son, as he himself said through the prophet: To do your will, O God, I desired (Ps. 39:9).
Leo the Great
This speech of the Head is the health of the whole body, this saying is instruction to the faithful, animates the confessor, crowns the martyr. For who could vanquish the hatred of the world, or the whirlwind of temptations, or the terrors of the persecutors, if Christ did not in all and for all say to the Father, Thy will be done. Let all the sons of the Church then utter this prayer, that when the pressure of some mighty temptation lies upon them, they may embrace endurance of the suffering, disregarding its terrors.
Hilary of Poitiers
Otherwise, He bare in His own body all the infirmities of us His disciples who should suffer, and nailed to His cross all wherein we are distressed; and therefore that cup cannot pass from Him, unless He drink it, because we cannot suffer, except by His passion.
Translation