In regard to the fulfillment of Zechariah 9:9-10, the Soncino Books of the Bible makes the terse comment that Rabbi Ibn Ezra considered this an allusion to Judas Maccabeus. Judas Maccabeus was the hero of the events surrounding the festival of Chanukah.
Consequently, Ibn Ezra sees the events of Zechariah 9:9-10 as fulfilled in the years 167-164 BC. However, Judas Maccabeus hardly fulfills the portrait of a gentle, humble king riding on a donkey.
Encyclopedia Judaica, in the article entitled Judah Maccabee makes these comments regarding him:
JUDAH MACCABEE, one of the great warriors of history, who laid the foundation of the future Hasmonean state…. His exceptional military talent made him the natural choice as military commander of the rebels, and the author of I Maccabees is unstinting in praise of his valor. … at the beginning of the struggle he succeeded in defeating a small Syrian force under the command of Apollonius, who was killed. Judah took possession of his sword which he used until his death as a symbol of vengeance… the Jewish commander succeeded in overcoming the numerically superior enemy in a great battle near Beth-Zur. This victory opened up the road to Jerusalem, which Judah entered at the head of his army.
Entering Jerusalem at the head of your army hardly fulfills Zechariah 9:9. Judah Maccabee is not the king of Israel predicted in Zechariah 9:9-10.