The purpose of the section breaks and headings in Daniel 11 is to indicate where we can expect to find some discontinuities in participant reference because the focus of the text has shifted to a different time period. For instance, "he" may not refer to the same person as in a previous verse. And there's likely been some shifting in the identities of the rulers referred to as "king of the north" and "king of the south."

The guidance for these headings comes from the work of Dan Bruce, available at https://goodnewsforjews.org/product/daniel-unsealed/. A key to Dan's understanding came from his taking a "time" as a span of time which hadn't yet been defined - and then piecing together the historical observations as a puzzle which then allows us to solve for that unknown variable. In terms of this historical puzzle, the cryptic expression "a time, times, and half a time" which sometimes has been taken to mean 3½ years, becomes the much longer span of 798 years from the desecration of the Temple by Antiochus IV in 167 BC to the beginning of the Muslim Caliphate in 632 AD, both of which were key events with respect to the status of Jerusalem and the Temple Mount. Then dividing this by 3½ to find out how long a "time" is, it's quite meaningful to find that it divides evenly, to a span of 228 years. And then when we've come to understand the lunar calendar and its 19-year cycles, this 228-year span takes on the additional significance of being made up of exactly 12 of these 19-year cycles.

Below is a fuller expansion of the information provided in the section headings, identifying time periods and participants where possible:

536-334 BC

Daniel 11:2

Current King of Persia = Cyrus the Great

King 1 of Persia = Cambyses II (r. 530-522)

King 2 of Persia = Smerdis (aka Gautama, r. 522-521)

King 3 of Persia = Darius I Hystaspes (aka Darius the Great, r. 521-486)

King 4 of Persia = Xerxes I (r. 486-465)

334-323 BC

Daniel 11:3

Alexander the Great arises, defeating Darius III Codomannus

at the Granicus River, 334 BC

at the Issus River, 333 BC

on the plains at Gaugamela, 331 BC

323-301 BC

Daniel 11:4

Alexander the Great dies at the height of his power, 323 BC,

with the empire then devolving into -

1) Cassander ruling Greece

2) Lysimachus ruling Asia Minor

3) Seleucus I Nicator ruling Persia and Babylon

4) Ptolemy I Soter ruling over Egypt and the land of Israel

301-253 BC, First Syrian War

Daniel 11:5

King of the south = Ptolemy I Soter

The one who becomes stronger = his son Ptolemy II Philadelphus

In the first Syrian War, 274-271 BC, Ptolemy II Philadelphus defeats Antiochus I Soter

253-246 BC, Second Syrian War

Daniel 11:6

King of the south = Ptolemy II

King of the north = Antiochus II Theos

Daughter of the king of the south who marries the king of the north = Berenice

246-223 BC, Third Syrian War

Daniel 11:7-9

The branch from her roots = Ptolemy III Euergetes, brother of Berenice

King of the north = Seleucus II

with Ptolemy III winning large quantities of gold and silver in tribute from Seleucus II

223-218 BC, Fourth Syrian War

Daniel 11:10

His sons, sons of the king of the north = Seleucus III Ceraunus, Antiochus III

217-204 BC, Battle of Raphia

Daniel 11:11-12

King of the south = Ptolemy IV

King of the north = Antiochus III

The multitude = the forces of Antiochus III

204-194 BC, Fifth Syrian War

Daniel 11:13-17

King of the north = Antiochus III

King of the south = Ptolemy V

"and he shall stand in the glorious land" = the forces of the north now have control over Judea and Jerusalem

"which by his hand shall be consumed" = looking ahead perhaps to what will happen under his son Mithridates/Antiochus IV

daughter of women = Cleopatra I, daughter of Antiochus III, who marries Ptolemy V

195-187 BC

Daniel 11:18-19

He = Antiochus III

The prince who eases his reproach - his debt to Rome = his son Mithridates

Antiochus III then dies in 187 BC while trying to reassert his authority in Persia

187-175 BC

Daniel 11:20-21

The raiser of taxes = Seleucus IV Philopater

The vile/contemptible person = Mithridates, who now manipulates himself into a position of power and renames himself Antiochus IV Epiphanes

175-168 BC, Sixth Syrian War

Daniel 11:22-28

He = Antiochus IV Epiphanes

The prince of the covenant = Onias III, high priest in Jerusalem

King of the south = Ptolemy VI Philometor

The great wealth of v 28 came from plundering Jerusalem on his way back from Egypt in 169 BC

168 BC - 67 AD

Daniel 11:29-35

v 30 - The ships of Kittim = ships of Cyprus which in 168 BC he captured but then were turned back against him.

On his retreat from Egypt back to Syria he stopped in Jerusalem to put down a revolt happening there,

after which began his prohibition of the practice of Judaism.

v 31 - The desecration of the altar of burnt offerings came soon afterwards, on day 25 of month 9 in 167 BC.

v 32 - The "people who know their God" are the Maccabees, through whom the daily sacrifices were resumed on day 25 of month 9 in 164 BC.

363 AD, First attempt to rebuild the Temple

Daniel 11:36-39

The King = Julian the Apostate

He seems to have had no real religious convictions.

He wrote blasphemous treatises whose purpose was to convince his subjects that the Christian religion was nothing but a hoax.

In order to oppose Christianity, he showed favor to the Jews.

He attempted to rebuild the Temple, but this was blocked by unexpected natural phenomena.

624-638 AD

Daniel 11:40a

Him = king of the Sassanid Empire, Chosroes II

King of the south = Mohammed and the nascent army of Islam

King of the north = emperor of the Byzantine Empire, Heraclius

602-616 AD

Daniel 11:40b-43a

He = Chosroes II

616-624 AD

Daniel 11:43b-44

He = Chosroes II

614-617 AD, Second attempt to rebuild the Temple

Daniel 11:45

He = Chosroes II