Jesus definitely fulfilled a lot of prophecies. Those which were vague he explained pretty well as to how he fulfilled them.
"I, the Lord, have called you in righteousness; I will take hold of your hand. I will keep you and will make you to be a covenant for the people and a light for the Gentiles" Isaiah 42:6
Jesus definitely fulfilled that one.
"Just as there were many who were appalled at him- his appearance was so disfigured beyond that of any man and his form marred beyond human likeness- so he will sprinkle many nations, and kings will shut their mouths because of him" Isaiah 52:14-15
That one too.
"Surely he took up our infirmities and carried our sorrows, yet we considered him stricken by God, smitten by him and afflicted. But he was pierced for our transgressions, he was crushed for our iniquities; the punishment that brought us peace was upon him, and by his wounds we are healed. We, all like sheep have gone astray, each of us has turned to his own way; and the Lord has laid on him the iniquity of us all" Isaiah 53:4-6
That's a difficult one to fulfill, but Jesus did.
"But you, Bethlehem Ephrathah, though you are small among the clans of Judah, out of you will come for me one who will be ruler over Israel, whose origins are from of old, from ancient times" Micah 5:2
Fulfilled.
"See your king comes to you, righteous and having salvation, gentle and riding on a donkey" Zechariah 9:9
Fulfilled.
"And I will pour out on the house of David and the inhabitants of Jerusalem a spirit of grace and supplication. They will look on me, the one they have pierced..." Zechariah 12:10
Fulfilled.
"Therefore my heart is glad and my tongue rejoices; my body also will rest secure, because you will not abandon me to the grave, nor will you let your Holy One see decay. You have made known to me the path of life; you will fill me with joy in your presence, with eternal pleasures at your right hand" Psalm 16:9-11
Fulfilled.
It is undeniable that fulfilling even these few scriptures in combination is not very easy, in fact, very improbable.