Daniel's original prophecy (Daniel 12:11; 9:27) has more than one fulfillment, as is often the case. The first took place in 168 BC, on the 25th day of the month Kislev (November-December in the Roman calendar). With the help of his army, Syrian king Antiochus Epiphanes erected an altar to the Greek god Zeus on the Temple Mount in Jerusalem and offered swine upon it. This intensified the Jewish resistance, leading to the Maccabean revolt. Once the Jews retook Jerusalem, they cleansed and rededicated the Temple in 165 BC, an act commemorated in the Jewish Hanukah celebration.
In 63 BC, the Roman general Pompey desecrated the Temple by brazenly entering the Holy of Holies, finding it empty. He did not plunder the Temple furnishings or treasury. The "abomination of desolation" Jesus mentions (Matthew 24:15) is the desecration of the Temple and the destruction of Jerusalem by the Roman armies in AD 70 after the Jews rebelled. The Temple was completely destroyed by the Roman legions, and not one stone was left on another, as Jesus prophesied (verse 2).
However, another fulfillment awaits. A short time before Christ returns, armies will once again surround Jerusalem and an "abomination" will be done in the city. As Matthew 24:21 says, this act inaugurates the time of Great Tribulation. At that time, the saints in Jerusalem are told to flee to the mountains for safety (Matthew. 24:16; Luke 21:20-21). What form this end-time abomination will take is not specifically mentioned, but it will likely be some action taken by the invading army Jesus mentions, possibly a blasphemous rite performed or an idol erected in the Temple precincts, as in the former desolations. (In the Old Testament, "abomination" is often synonymous with "idol.") It could also be something as simple as the army's brutal destruction of the Temple Mount and its buildings. Notwithstanding, the abomination of desolation is one of the chief signs of the end time that Christians are commanded to watch (Matthew 24:42-44; Luke 21:34-36).