And the city of Jerusalem shall be trampled underfoot for 42 months

First Jewish-Roman War Timeline (click to enlarge)

But leave out the court which is outside the temple, and do not measure it, for it has been given to the Gentiles. And they will tread the holy city underfoot for forty-two months.

This timeline outlines the movements of Roman legions — primarily Legio V Macedonica, X Fretensis, XV Apollinaris, and the ill-fated XII Fulminata — during the First Jewish-Roman War (66 – 70 CE) based on the account of Flavius Josephus. 1, 2.

66 CE: Initial Revolt and Roman Failure 1., 2., 3

May 66: The revolt begins in Caesarea and spreads to Jerusalem; the Roman garrison in Jerusalem is killed.
October – November 66: Cestius Gallus, Legate of Syria, leads the XII Fulminata and auxiliary troops from Syria into Judea.
November 66: Cestius is defeated by Jewish forces at the Pass of Beth-Horon while retreating. The XII Fulminata suffers heavy casualties and loses its eagle standard. 1, 2, 3, 4, 5.

67 CE: The Galilean Campaign (Vespasian) 1, 2

Vespasian is appointed commander and gathers three legions (V, X, XV) at Ptolemais (Akko). 1

Spring (May) 67: Roman troops invade Galilee. Sepphoris surrenders and is garrisoned.
June – July 67: Jotapata (Yodfat) is besieged by Vespasian with ~60,000 men, resulting in the city’s fall after 47 days and the capture of Josephus.
Summer 67: Titus captures Japha and subdues Mount Gerizim (Samaria).
September 67: Titus captures Tarichaeae on the Sea of Galilee. Surviving rebels are executed or sold into slavery.
October – November 67: Gamla (Golan) is besieged and falls to the Romans after 6 weeks.
Late 67: Gischala surrenders. John of Gischala flees to Jerusalem.
Winter 67/68: Roman troops winter in Caesarea and Scythopolis. 1, 2., 3, 4, 5

68 CE: Subjugation of the Coast and Perea 1

Spring 68: Vespasian moves south, capturing Antipatris, Lydda, and Jamnia.
April – May 68: Roman troops move to Emmaus (Legio V stationed here) and Bethleptepha, raiding Idumaea.
June 68: Romans capture Jericho and garrison it.
June 68: News of Nero’s death arrives; Vespasian pauses the advance on Jerusalem to await developments. 1, 2, 3

69 CE: Interregnum and Political Shift

Spring 69: Vespasian resumes campaigns in the highlands, taking Gophna, Bethel, and Ephraim.
June 69: Romans under Cerialis destroy Hebron and burn upper Idumaea.
July 69: Vespasian is proclaimed emperor in Caesarea.
Late 69: Vespasian departs for Rome, leaving Titus in command to finish the war. 1

70 CE: The Siege of Jerusalem (Titus) 1*%2066%E2%80%9373%20CE:%20First%20Jewish%2DRoman%20War%2C%20with,X%20Fretensis%20is%20garrisoned%20in%20the%20city., 2*%2066%E2%80%9373%20CE:%20First%20Jewish%2DRoman%20War%2C%20with,X%20Fretensis%20is%20garrisoned%20in%20the%20city.

Titus gathers four legions (V, X, XII, XV) for the final assault. 1, 2., 3.

April (Passover) 70: Titus advances from Caesarea and sets up camp at Mount Scopus (Northeast of Jerusalem).
April – May 70: The Legio X Fretensis sets up on the Mount of Olives. The First (outer) Wall is breached in late May.
June 70: Romans build siege works and attack the inner walls.
July (July 24) 70: The Antonia Fortress is taken and destroyed.
August (August 29/30) 70: The Second Temple is burned, and the Romans occupy the Temple Mount.
September 70: The Upper City is taken. Jerusalem is fully captured and razed on or around September 8th. 1, 2, 3, 4