I find that all 6 items were fulfilled, 100%. The prophecy has to do with the end of Israel under the Law, when their sins became so bad that they rejected their own Messiah. That's when Jesus provided redemption and atonement for their sins. It was a major prophecy of the OT.
We know it was all fulfilled because immediately after the end of this 69.5 Week period, the city and the sanctuary was to be destroyed. This happened in 70 AD by the Roman Army. All 6 items promised in Dan 9.24 were fulfilled in the Messiah, Jesus.
Dan 9.24 “Seventy ‘sevens’ are decreed for your people and your holy city to finish transgression, to put an end to sin, to atone for wickedness, to bring in everlasting righteousness, to seal up vision and prophecy and to anoint the Most Holy Place."
The prophecy ranged from the restoration of Israel from the Babylonian Captivity to the time of Christ, from one destruction of Jerusalem to another, the other taking place in 70 AD.
It finished transgression by condemning for all time the sin of Israel under the Law. Their covenant with God under the Law of Moses was terminated, and under that system they were permanently divorced.
It put an end to sin because Israel was consigned to final punishment, and they were completely removed from their land as the people of God. No sin could be there because they were no longer there as God's People.
It atoned for wickedness because Christ died to show the full depth of Israel's sin, thereby satisfying God's rage against them. God showed the full extent of His contempt for Israel by allowing His own Son to be murdered, fully exposing their sin.
It brought in everlasting righteousness because Christ rose from the dead, establishing his righteousness in men for all time. It could never be expunged.
It fulfilled prophecy because it was foretold that Messiah would come to open up a way of righteousness to lead Israel to everlasting salvation.
It anointed the Most Holy because Jesus himself was anointed as the eternal temple of God, through whom all Israel could obtain redemption from sin.