Daniel 9:27 has Dual Fulfillment (Part 1)
The first, most important and primary fulfillment of 'the covenant' of Daniel 9:27 was by the Lord Jesus Christ, confirming it at Calvary with His own blood. EAR, Kay, and Kevin Heckle have all posted on this recently and I want to add my agreement, as well as state that I believe there is dual fulfillment in this verse. Daniel 9:2 states that Daniel had been reading the book of Jeremiah, and 'the covenant' is stated in Jeremiah 31:31-34. 'Behold, the days come, saith the LORD, that I will make a new covenant with the house of Israel, and with the house of Judah: Not according to the covenant that I made with their fathers in the day [that] I took them by the hand to bring them out of the land of Egypt; which my covenant they brake, although I was an husband unto them, saith the LORD: But this [shall be] the covenant that I will make with the house of Israel; After those days, saith the LORD, I will put my law in their inward parts, and write it in their hearts; and will be their God, and they shall be my people. And they shall teach no more every man his neighbour, and every man his brother, saying, Know the LORD: for they shall all know me, from the least of them unto the greatest of them, saith the LORD: for I will forgive their iniquity, and I will remember their sin no more.'
This was the covenant that Daniel had just read in Jeremiah, and this was the covenant he was looking for fulfillment of when he prayed. The last two verses of Daniel's prayer were Dan 9:18-19 'O my God, incline thine ear, and hear; open thine eyes, and behold our desolations, and the city which is called by thy name: for we do not present our supplications before thee for our righteousnesses, but for thy great mercies. O Lord, hear; O Lord, forgive; O Lord, hearken and do; defer not, for thine own sake, O my God: for thy city and thy people are called by thy name.'
At this point in Daniel's prayer, the angel Gabriel arrives to give Daniel the prophesy contained in Daniel 9:24-27. Gabriel does not correct Daniel about the covenant that is in context, but just gives the prophesy and in verse 27 even mentions 'the covenant', which obviously must be the one Daniel had read, was looking for, and had prayed about, that one in Jeremiah 31:31-34.
Dan 9:24-27 'Seventy weeks are determined upon thy people and upon thy holy city, to finish the transgression, and to make an end of sins, and to make reconciliation for iniquity, and to bring in everlasting righteousness, and to seal up the vision and prophecy, and to anoint the most Holy. Know therefore and understand, [that] from the going forth of the commandment to restore and to build Jerusalem unto the Messiah the Prince [shall be] seven weeks, and threescore and two weeks: the street shall be built again, and the wall, even in troublous times. And after threescore and two weeks shall Messiah be cut off, but not for himself: and the people of the prince that shall come shall destroy the city and the sanctuary; and the end thereof [shall be] with a flood, and unto the end of the war desolations are determined. 27 And he shall confirm the covenant with many for one week: and in the midst of the week he shall cause the sacrifice and the oblation to cease, and for the overspreading of abominations he shall make [it] desolate, even until the consummation, and that determined shall be poured upon the desolate.'
The Lord Jesus Christ proclaimed Himself as Messiah to the people of Israel at the synagogue in Nazareth at the beginning of His ministry when He read messianic scriptures and said that they were fulfilled in their ears 'this day'. The people understood what He was saying and tried to kill Him. Then, around three and one-half years later, in the 'midst of the week' at Calvary, He confirmed 'the covenant' with His own blood, dying for the sins of the 'many'. Then, He rose from the dead the third day, making the forgiveness of sins and the remembering of them 'no more' in the covenant of Jeremiah 31:31-34 possible. By so doing He caused the temple sacrifices and oblations to 'cease' in effectiveness before the throne of God, and that was evidenced by the veil of the Holy of Holies rent in two. The majority of Jews rejected the Gospel, so after the martyr of Stephen, the Gospel then went to the Gentiles. For the rejection of the Lord Jesus Christ and the murder and persecution of His followers ('abominations'), Jerusalem and the temple were destroyed (made 'desolate'), and many of the Jews were killed and the rest were scattered ('poured upon the desolate') by the Roman Army in 70 A.D. just as Christ had predicted, fulfilling Daniel 9:27 the first time.