The interpretation timeline
Matthew 9:17 Douay-Rheims

Neither do they put new wine into old bottles. Otherwise the bottles break, and the wine runneth out, and the bottles perish. But new wine they put into new bottles: and both are preserved.

A.D. 908 – 1863 5 witnesses

Medieval

c. 750 – 1100
908
A.D.
c. A.D. 841–908
“After two comparisons made, that of the wedding, and that of the undressed cloth, He adds a third concerning wine skins; Neither do men put new wine into old skins. By the old skins He means His disciples, who were not yet perfectly renewed. The new wine is the fulness of the Holy Spirit, and the depths of the heavenly mysteries, which His disciples could not then bear; but after the resurrection they became as new skins, and were filled with new wine when they received the Holy Spirit into their hearts. Whence also some said, These men are full of new wine. (Acts 2:13.)”
Source

Scholastic

c. 1100 – 1500
1256
A.D.
Thomas Aquinas Catholic
1225–1274
“Here the question about the feast is set forth, and the answer follows, where it says "And Jesus said to them." But here there is a literal question: why do Mark 2:18 and Luke 5:29 seem to show that the question was put by others — where it is said in Mark 2:18: "Why do the disciples of John and of the Pharisees fast, but your disciples do not fast?" Therefore the disciples themselves did not ask it. Augustine resolves this. It was thus: the Pharisees were laying snares for Christ, and so at one time they brought the Herodians with them, but at another they took up the disciples of John. Hence the question could have been put both by others and by the disciples. But whence came it that they fasted? The answer given here is: from their own traditions, or from the Law, as it is recorded that on the Day of Atonement they were bound to fast. And Zechariah 8:19: "The fast of the fourth month, and the fast of the fifth, and the fast of the seventh, and the fast of the tenth shall be to the house of Judah joy and gladness, and great solemnities." Likewise the disciples of John fasted after the example of their master, who was of great austerity; but the disciples of Christ did not fast. "And Jesus said to them." Here Jesus answers, and subtly. First he assigns the reason on his own part, then on the part of the disciples. Concerning the first he does two things: first he determines the time for feasting; second, the time for fasting, where it says, "But the days will come when the bridegroom shall be taken away from them, and then they shall fast." He says, therefore: "Can the children of the bridegroom mourn as long as the bridegroom is with them?" Where this Evangelist says "mourn," another says "fast"; for although fasting has a certain spiritual joy, nevertheless, as is said in Hebrews 12:11, "all discipline for the present indeed seems not to be a matter of joy, but of sorrow." Hence there is a fasting of spiritual joy, as is said in Daniel 9:3: "I set my face to the Lord my God, to pray and to make supplication, in fasting, sackcloth, and ashes." There is likewise a fasting of mourning and affliction, as when it is undertaken on account of sorrows. The Lord answers concerning both. For Christ is the bridegroom: whoever has a bride is a bridegroom. For he himself is the bridegroom of the whole Church, and its beginning. The old Law had one beginning, and the new Law another; for the old Law had its beginning in fear, the new Law in love; hence Romans 8:15: "For you have not received the spirit of bondage again in fear, but you have received the spirit of adoption of the sons of God." And Hebrews 12:22: "You have come to Mount Sion, and to the city of the living God, Jerusalem." Since, therefore, the beginning of the new Law was in love, he had to nourish his disciples in a certain love; therefore he calls himself the bridegroom, and the disciples sons, because these are names of love. Hence it is good that I should preserve them; and therefore I do not wish to impose anything heavy upon them, lest they be repelled and so fall back. And therefore those who are new in the religious life are not to be burdened. Hence Ambrose, in the Book of Similitudes, rebukes those who burden novices heavily. And this is what Christ says: "Can the children of the bridegroom mourn?" etc., as if to say: it is not fitting that they should fast, but rather that they should live in a certain sweetness and love; so that thus they may receive my law in love, as is said in Romans 6:4: "As Christ rose from the dead by the glory of the Father, so we also may walk in newness of life." Hence from Easter until Pentecost no fasts are observed, because then the Church calls to mind the newness of the Law. "But the days will come," etc. And this is to be taken literally. "The days will come," namely when, through your contriving, the bridegroom shall be taken away from them; and then they shall fast. And he foretold this to them, saying in John 16:20: "You shall weep, but the world shall rejoice." For those who lived before Christ desired the presence of Christ, as Abraham, and Isaiah, and the other prophets. Likewise after his death he was desired by the apostles: hence Peter was as it were in continuous grief on account of the absence of Christ; and Paul said, "I desire to be dissolved and to be with Christ." Hence that was the time for fasting. Another reason why they were not bound to fast in his presence is that fasting is to be chosen insofar as it chastises the flesh, lest it grow too strong against the spirit; but while he was present, he kept them from excess; therefore it was not necessary for them to fast; hence in John 17:12: "Father, while I was with them, I kept them." But John the Baptist did not have this power, and therefore his disciples had to fast. But when Christ was taken away, they had to fast. Hence Paul says in 1 Corinthians 9:27: "I chastise my body, and bring it into subjection," etc. "But no one puts a patch of unshrunk cloth upon an old garment." Here he sets forth another reason on the part of the disciples, and he gives two examples: one according to Augustine, the other according to Jerome. According to Augustine, then, he means to say: it has been said that in the presence of Christ the disciples ought not to fast, nor indeed by reason of their own condition, because heavy things ought not to be imposed on the imperfect. Since, therefore, these men are imperfect, fasting ought not to be imposed on them. To signify this, then, he touches on it under the metaphor of cloth and wine. Because righteousness consists in exterior works and in a newness of affection, he therefore gives two examples. He says, then, "no one puts," etc., as if to say: if one wished to join on new cloth, he would not put a patch — that is, a piece — of unshrunk cloth, that is, new cloth, upon an old garment, because it would take away its beauty; so likewise, if some imperfect person has a certain custom in his manner of life, if you wish to impose upon him a different yoke, he draws back from what he had been accustomed to, and the tear becomes worse, as is said below. "Neither do they put new wine into old wineskins." Here he gives another example, from wine, as if to say: my disciples are like old wineskins. The new wine is the new Law, by reason of its newness: hence, when they had received the Holy Spirit, they were said to be full of new wine, Acts 2:13. Hence "neither do they put new wine into old wineskins; otherwise the wineskins burst." Hence if you impose a new manner of living upon an old man, who for some time has had a certain custom, his heart is burst through intolerance. Likewise "the wine is spilled out," that is, it is not kept safe, "and the wineskins are lost": because they trampled upon the commandments of God, and therefore they perish. "But they put new wine into new wineskins," renewing spiritual teaching through the affections, as the Apostle says in 1 Corinthians 2:13: "comparing spiritual things with spiritual." Proverbs 2:10: "If wisdom shall enter into your heart, and knowledge shall please your soul, counsel shall keep you, and prudence shall preserve you, that you may be delivered from the evil way, and from the man that speaks perverse things," etc. Jerome expounds it otherwise: for he calls the institution of the Pharisees the old garment, and calls the evangelical teaching the new; as if to say, it is not good that they should keep to your precepts, because in that way they would make the old tears worse, and thus they would not be able to receive the new teaching, just as we see that one who is not imbued with a contrary teaching more easily receives his own teaching than one who is already imbued with it. And therefore it is not good that your disciples be imbued with your teaching.”

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“While he spake these things unto them,.... To the Scribes and Pharisees, and to John's disciples, concerning, and in vindication of his, and his disciples, eating and drinking with publicans and sinners, and their not fasting as others did; and while he spake these parables, to expose the folly of self-righteous persons, and justify his own conduct, in calling sinners to repentance, behold, there came a certain ruler and worshipped him. This man, as both Mark and Luke say, was named Jairus; and was a ruler, not of the sanhedrim, or lesser consistory, but of the synagogue that was at Capernaum; and whom the Jews call, , "the head of the synagogue". Mark says, he was "one of the rulers": not that there were more rulers than one, in one synagogue (q): but as in great cities, so it is likely in Capernaum there were more synagogues than one, of which he was one of the rulers: so we read of (r), "heads", or "rulers of synagogues". As this is one mistake, so it is another to say, that Dr. Lightfoot speaks of this ruler, as the same with the "minister" of the congregation; when both here, and in the place referred to, he manifestly distinguishes them; as do the Jews: for, by this ruler, as their commentators (s) say, "the necessary affairs of the synagogue were determined, as who should dismiss with a prophet, who should divide the "shema", and who should go before the ark.'' Whereas the business of , "the minister of the synagogue", was to bring in and out the ark, or chest, in which was the book of the law; and particularly, when the high priest read, or pronounced the blessings, "he" took the book, and gave it to "the ruler of the synagogue"; and the ruler of the synagogue gave it to the "sagan", and the "sagan" to the high priest (t). The doctor makes indeed , "the messenger of the congregation", to be the same with "the minister of the synagogue", and which is his mistake; for these were two different officers (u): the former was the lecturer, or preacher; and the latter, a sort of a sexton to keep the synagogue clean, open and shut the doors, and do other things before mentioned. This Jairus was a man of great power and significance; who in such a very humble manner prostrated himself at the feet of Jesus, and expressed such strong faith in him: saying, my daughter is even now dead, but come and lay thine hand upon her, and she shall live. Luke says, she was "his only daughter": and Mark calls her his "little daughter": though both he and Luke say, she was about "twelve" years of age, and that with strict propriety, according to the Jewish canons, which (w) say; that "a daughter, from the day of her birth until she is twelve years complete, is called "a little one" and when she is twelve years of age, and one day and upwards, she is called "a young woman".'' Her case seems to be differently represented; Mark says, she was "at the point of death", or "in the last extremity"; and Luke, that she "lay dying": but Matthew here says, that she was "even now dead", which may be easily reconciled: for not to observe, that signifies "near", and the phrase may be rendered, "she is near dead", or just expiring, the case was this; when Jairus left his house, his daughter was in the agony of death, just ready to give up the ghost; so, that he concluded, by the time he was with Jesus, she had made her exit; as it appears she had, by a messenger, who brought the account of her death, before they could get to the house. The ruler's address to Christ on this occasion, is a very considerable, though not so great an instance of faith as some others; that he, who was a ruler of a synagogue, should apply to Christ, which sort of men were generally most averse to him; that he should fall down and worship him, if not as God, since as yet he might be ignorant of his deity, yet behaved with the profoundest respect to him, as a great man, and a prophet; that he should come to him when his child was past all hope of recovery; yea, when he had reason to believe she was actually dead, as she was; that even then, he should believe in hope against hope; he affirms, that he really believed, that if Christ would but come to his house, and lay his hand upon her, an action often used in grave and serious matters, as in blessing persons, in prayer, and in healing diseases, she would certainly be restored to life again. (q) Vid. Rhenfurd. de decem otiosis dissert. 2. c. 7. (r) T. Bab. Gittin, fol. 60. 1. (s) Jarchi & Bartenora in Misn. Yoma, c. 7. sect. 1. & Sota, c. 7. sect. 7. (t) Misn. Sota, c. 7. sect. 7. & Bartenora in ib. (u) Vid. Rhenfurd, dissert. 1. p. 81, etc. (w) Maimon. Hilchot lshot, c. 2. sect. 1. & Bartenora in Misn. Nidda, c. 5. sect. 6.”
Source
1849
A.D.
1774–1849
“New wine into old bottles. [3] These vessels were made of skins, or were leather bottles, in which wine used to be carried and kept. (Witham) — They were made of goat-skins prepared and sewed together, as is common in Spain and other southern countries to this day. (Haydock) — They were to wait till they were renewed by the Holy Ghost, before they could enter with advantage on the hard ways of penance. (Bible de Vence)”
Source
1863
A.D.
1796–1863
“Skins or bags were used, as is still the case in Asia. When new wine fermented in old skins, these not being easily distended, were apt to burst. This, however, St. Chrysostom remarks, does not arise from the wine, or from the skins in which it is received, but from the haste of those who put it in. He adds, that " Christ foretells that His disciples will hereafter be renewed in spirit ; and that until this take place, no- thing austere, or burthensome, should be enjoined on them." In loc.”
Source
Modern · 1953 →

The in-app commentary runs from the Fathers to the early-modern record, then stops — that's where the public-domain sources end, not where the reading does. For the modern reading, follow the sources directly.