Ashkelon, located at the south of the coastal plain, was an important Canaanite city mentioned in ancient Egyptian sources.
For many years, Ashkelon was under Egyptian rule. During the era of the Judges, Philistines settled in the area. According to the books of Yehoshua and Shoftim, Ashkelon was designated as part of the tribal portion of Yehuda, but Yehuda failed to conquer it (Joshua 13, 1-3; Judges 1, 18).
Shimshon descended to Ashkelon after he killed thirty Philistines and took their garments after his riddle was “solved” by his Philistine companions in Timna (Judges 14, 19).
During the period of Assyrian rule, Ashkelon was subject to the Assyrian Empire. Ashkelon cooperated with King Hizkiyahu of Yehuda in his rebellion against Assyria. In response, the Assyrians conquered Ashkelon and exiled its king (according to Assyrian documents).
In later times, King Nebuchadnezzar of Babylonia conquered Ashkelon and exiled its king to Babylonia (according to Babylonian documents).

Ashkelon. Z.Radovan/BibleLandPictures.com