All dates listed directly appear in the film in some type of written form, or they have been concretely verified through calendar search and date conversion.
• Sep. 24, 1953 — Chan Lok-kwan is born [fake ID; birth certificate].
(The false date of issue on the ID is Feb. 5, 1983.)
• Oct. 2nd, 1984 — Lok-kwan runs from Big Boss and Wong Gau, enters the Walled City, and meets Cyclone and Shin [Cyclone's shop calendar].
• Oct. 3rd, 1984 — Lok-kwan meets AV, and starts work in the Walled City [debt promise letter signed in AV's clinic].
• Oct. 17, 1984 — Lok-kwan delivers propane to Cyclone's shop, now working multiple jobs and sleeping on roofs [Cyclone's shop calendar].
(With the context of dates before and after, this could be Oct. 17 or Nov. 17, 1984. I went with Oct. 17 based on the length/placement of the white-on-green day text beneath the date number, as the month itself can't easily be made out. Oct. 17 was a Wednesday while Nov. 17 was a Saturday, so the former would take up more character space as shown in the screencap.)
• Dec. 5, 1984 — Cyclone treats Lok-kwan to char siu rice, and offers him a place to live [BBQ restaurant calendar].
• Dec. 19, 1984 — Signing of the Sino-British Joint Declaration [BBQ restaurant calendar; history].
• Dec. 31, 1984 — The Walled City Four set up the karaoke machine. Lok-kwan tells Cyclone he wants to stay in the Walled City [Cyclone's shop calendar].
• Jan. 10, 1985 — Chau-gor and Tiger-gor storm into the Walled City to kill Lok-kwan. Big Boss and Wong Gau make a deal with Chau-gor to finish the job, and attack the Walled City. Cyclone dies. Big Boss takes over the Walled City and locks up Chau-gor [BBQ restaurant calendar; Cyclone's shop calendar].
• Jan-Apr 1985 — 3 month timeskip. Lok-kwan has been recovering from his wounds, and attempting to sort out his immigrant status. Shin, Twelve, and AV are in hiding/exile [onscreen text].
• Aug. 30, 1985 — Ghost Festival. Lok-kwan, Shin, Twelve, and AV have their final showdown with Wong Gau, and take back the Walled City [set pieces; history].
BONUS:
• Jan. 26, 1957 — Ah-Jim sneaks into Cyclone's new barber shop in the Walled City, and tells Cyclone that his wife is pregnant with Lok-kwan [converted from Chinese calendar date in the shop].
(Given that this is set after Lok-kwan's given birthdate, unfortunately it is a chronological inconsistency, although admirably the only apparent one in the film. The Chinese date on the calendar is Bingshen Year, 26th day of the 12th month.)
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