Judith Beheading Holofernes, by Artemisia Gentileschi

Although the details are anachronistic, the story of Judith is associated with Hanukkah because a heroic individual challenges a cruel and overwhelming oppressor. Here's an earlier version:

According to ancient Jewish sources, during the period of Syrian rule, Syrian officers in Israel had the authority to rape all Jewish brides. The bride would be allowed to marry her husband only after submitting to the Syrian officer.

Various Midrash (rabbinic commentaries on the scriptures) tell the story of how a bride’s family defended her on her wedding day, and killed the Syrian rapist and his soldiers. Enraged, the Syrian king besieged Jerusalem. A Jewish widow went out to the king, and sought an audience with him. She seduced him, got him drunk, and then decapitated him with his own sword. She placed his head in a bag, and took it back to the city walls, where the Jews displayed it prominently. The Syrian army, deprived of its leader, panicked and fled.

Judith Beheading Holofernes, Caravaggio, c. 1598

Judith and her maid, tiptoeing away after the deed, by Gentileschi (a little after Caravaggio):

. . . . the battle is a rout, in favor of Israel, though Sisera has received aid from all the Kings of Canaan, who likewise wish to destroy Israel. Israel receives miraculous aid from the forces of Nature, caused of course by their Director. The stars approach the battlefield, scalding the army of Sisera, and causing them to seek refuge in the waters of the Brook of Kishon. But those waters, usually shallow, miraculously rise and drown all the forces of Sisera - that is, all but him.

Sisera, shocked and stunned by the outcome of the battle, staggers in the direction of the Tent of Chever the Kenite, who has a peace treaty with Yavin, the overall King of Canaan. Chever's wife, Yael, emerges from the tent and gestures to him to come into her tent for protection. She plies him with milk and butter, and he falls asleep. She seizes a tent peg and a hammer, and drives the peg between his eyebrows, through his head and into the ground, definitely and thoroughly killing him. When Barak, in hot pursuit of Sisera, arrives, Yael says, "the one you are looking for is in my tent, and he is quite dead."