Verse 25:[1] And they took (Judg. 8:3; Ps. 83:11) two princes of the Midianites, Oreb and Zeeb; and they slew Oreb upon (Is. 10:26) the rock Oreb, and Zeeb they slew at the winepress of Zeeb, and pursued Midian, and brought the heads of Oreb and Zeeb to Gideon on the other side Jordan.
[He killed Oreb] There were no ransoms that might prevent the killing of the captives. See Concerning the Law of War and Peace[2] 3:4:10. See Judges 8:18 (Grotius).
[At the winepress[3]] On the plain (the Chaldean in Vatablus). It is likely that they escaped to these places seeking hiding places (Bonfrerius).
[Across the streams of Jordan, מֵעֵ֖בֶר לַיַּרְדֵּֽן׃] On the other side, or beyond, Jordan (Pagnine, Vatablus), on the eastern side (Vatablus). They observe that at that time already Gideon with his men, in pursuing the enemy, had crossed Jordan, as it is evident from Judges 8:4 (Malvenda). Therefore, these things are said by way of prolepsis, or anticipation (Malvenda, Vatablus).
To Gideon on the other side Jordan: For Gideon in the pursuit had passed over Jordan, as we read, Judges 8:4, which, though mentioned after this, may seem to have been done before it, such transpositions being frequent in sacred story. Or, on this side Jordan, for the Hebrew word is indifferent to both sides: see Genesis 50:10.[4] And so this is opposed to what follows of his passing over Jordan, Judges 8:4. And then there is no anticipation here.
[1] Hebrew: וַֽיִּלְכְּד֡וּ שְׁנֵֽי־שָׂרֵ֙י מִדְיָ֜ן אֶת־עֹרֵ֣ב וְאֶת־זְאֵ֗ב וַיַּהַרְג֙וּ אֶת־עוֹרֵ֤ב בְּצוּר־עוֹרֵב֙ וְאֶת־זְאֵב֙ הָרְג֣וּ בְיֶֽקֶב־זְאֵ֔ב וַֽיִּרְדְּפ֖וּ אֶל־מִדְיָ֑ן וְרֹאשׁ־עֹרֵ֣ב וּזְאֵ֔ב הֵבִ֙יאוּ֙ אֶל־גִּדְע֔וֹן מֵעֵ֖בֶר לַיַּרְדֵּֽן׃
[2] De Jure Belli ac Pacis.
[3] Hebrew: בְיֶקֶב.
[4] Genesis 50:10: “And they came to the threshingfloor of Atad, which is beyond Jordan (אֲשֶׁר֙ בְּעֵ֣בֶר הַיַּרְדֵּ֔ן), and there they mourned with a great and very sore lamentation: and he made a mourning for his father seven days.”
Psalm 83: <A Song or Psalm of Asaph.> Keep not thou silence, O God: hold not thy peace, and be not still, O God. 2 For, lo, thine enemies make a tumult: and they that hate thee have lifted up the head. 3 They have taken crafty counsel against thy people, and consulted against thy hidden ones. 4 They have said, Come, and let us cut them off from being a nation; that the name of Israel may be no more in remembrance. 5 For they have consulted together with one consent: they are confederate against thee: 6 The tabernacles of Edom, and the Ishmaelites; of Moab, and the Hagarenes; 7 Gebal, and Ammon, and Amalek; the Philistines with th…
Matthew Henry: 'Two of the chief commanders of the host of Midian were taken and slain by the Ephraimites on this side Jordan, Judges 7:25. Their names perhaps signified their nature, Oreb signifies a raven, and Zeeb a wolf (corvus and lupus). These in their flight had taken shelter, one in a rock (Isaiah 2:21; Revelation 6:15), the other by a winepress, as Gideon for fear of them had lately hid his corn by a winepress, Judges 6:11. But the places of their shelter were made the places of their slaughter, and the memory of it was preserved to posterity in the names of the places, to their perpetual infamy: Here fell the princes of Midian.'
Hebrew students, Poole's interpreters seem to think that Oreb and Zeeb were killed in Palestine, and that their heads were brought to Gideon, who was already on the other side of Jordan. Poole himself (in bold) seems to think otherwise. Have a look at the Hebrew. What do you think?