The interpretation timeline
Matthew 9:16 Douay-Rheims

And nobody putteth a piece of raw cloth unto an old garment. For it taketh away the fullness thereof from the garment, and there is made a greater rent.

A.D. 407 – 1849 6 witnesses

Patristic

before A.D. 750
407
A.D.
John Chrysostom Patristic
A.D. 347–407
“Here again He confirms what He has said by examples of common things; No man putteth a patch of undressed cloth into an old garment; for it taketh away its wholeness from, the garment, and the rent is made worse; which is to say, My disciples are not yet become strong, but have need of much consideration; they are not yet renewed by the Spirit. On men in such a state it is not behoveful to lay a burden of precepts. Herein He establishes a rule for His disciples, that they should receive with leniency disciples from out of the whole world.”
Source

Medieval

c. 750 – 1100
908
A.D.
c. A.D. 841–908
“By the old garment He means His disciples, who had not yet been renewed in all things. The patch of undressed, that is, of new cloth, means the new grace, that is, the Gospel doctrine, of which fasting is a portion; and it was not meet that the stricter ordinances of fasting should be entrusted to them, lest they should be broken down by their severity, and forfeit that faith which they had; as He adds, It taketh its wholeness from the garment, and the rent is made worse.”
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
“Neither do men put new wine into old bottles,.... As in the former parable, our Lord exposes the folly of the Scribes and Pharisees, in their zealous attachment to the traditions of the elders; so in this, he gives a reason why he did not call these persons by his Gospel, who were settled upon the old principle of self-righteousness, but sinners, whom he renews by his Spirit and grace: for by "old bottles" are meant, the Scribes and Pharisees. The allusion is to bottles, made of the skins of beasts, which in time decayed, waxed old, and became unfit for use: such were the wine bottles, old and rent, the Gibeonites brought with them, and showed to Joshua, Jos 9:4 and to which the Psalmist compares himself, Psa 119:83 and which the Misnic doctors call and their commentators (o) say, were , "bottles made of skin", or "leather", and so might be rent. Of the use of new and old bottles, take the following hint out of the "Talmud" (p). "The bottles of the Gentiles, if scraped and "new", they are free for use; if "old", they are forbidden.'' Now the Scribes and Pharisees may be signified by these old bottles, being natural men, no other than as they were born; having never been regenerated, and renewed in the spirit of their minds; in whom the old man was predominant, were mere formal professors of religion, and self-righteous persons: and by "new wine" is meant, either the love and favour of God compared to wine, that is neat and clean, because free from hypocrisy in him, or motives in the creature; to generous wine, for its cheering and reviving effects; and to new wine, not but that it is very ancient, even from everlasting, but, because newly manifested, in the effectual calling and conversion: or the Gospel is signified by wine, for its purity, good flavour, and pleasant taste; for its generous effects, in reviving drooping spirits, refreshing weary persons, and comforting distressed minds; and by new wine, not that it is a new doctrine, an upstart notion, for it is an ancient Gospel, but because newly and more clearly revealed by Christ and his apostles: or the blessings of grace which spring from the love of God, and are manifested in the Gospel, such as pardon of sin, reconciliation and atonement, justifying and sanctifying grace, spiritual joy and peace, and the like. Now as the new wine is not put into old bottles, else the bottles break, and the wine runneth out, and the bottles perish: so the love of God, the Gospel of the grace of God, and the blessings of it, are not received and retained, nor can they be, by natural men, by self-righteous persons: they do not suit and agree with their old carnal hearts and principles; they slight and reject them, and let them run out, which proves their greater condemnation. But they put new wine into new bottles, and both are preserved. By "new bottles" are meant sinners, whom Christ calls by his grace, and the Spirit regenerates and renews, who are made new creatures in Christ; who have new hearts, and new spirits, and new principles of light, life, love, faith, and holiness, implanted in them; who have new eyes to see with, new ears to hear with, new feet to walk with, to and in Christ, new hands to work and handle with, and who live a new life and conversation. Now to such as these, the love of God is manifested and shed abroad in their hearts; by these, the Gospel of Christ is truly received and valued, and these enjoy the spiritual blessings of it; and so both the doctrine of the Gospel, and the grace of God, are preserved entire, and these persons saved in the day of Christ. (o) Jarchi & Bartenora in Misn. Celim, c. 24. sect. 11. & Negaim, c. 11. sect. 11. (p) T. Bab. Avoda Zara, fol. 33. 1.”
Source
1849
A.D.
1774–1849
“A piece of raw cloth. [2] By the Greek is signified new-woven cloth, that has not yet passed the hands of the fuller. (Witham) — And no one putteth, &c. Christ, by these similitudes, justifies the manner of life which he taught his disciples, which at first was adapted to their understandings; lest, if in the beginning, he had required them to fast contrary to what they had been accustomed, they might have been frightened at the austerity of his institute, and deserted him. He compares, therefore, his disciples to an old garment, and to old bottles; and an austere mode of life to new clothes and new wine. And he argues, that if we do not put new cloth to an old garment, because it tears the garment the more, nor put new wine into old bottles, because by its fermentation it would easily break them, so in like manner his disciples, who had been accustomed to a less rigid mode of life, were not at once to be initiated into an austere discipline, lest they should sink under the difficulty, and relinquish the pursuit of a more perfect life. (Menochius)”
Source

Undated

date unknown
date
unknown
Glossa Ordinaria Medieval
“(ap. Anselm.) As much as to say, An undressed patch, that is, a new one, ought not to be put into an old garment, because it often takes away from the garment its wholeness, that is, its perfection, and then the rent is made worse. For a heavy burden laid on one that is untrained often destroys that good which was in him before.”
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.