From "BYTE" magazine of July 1998:

Year 2000 Survival Guide, The Millennium Bug

Time Line: Chronicle of the Slow Collision

1993
Boeing notes errors in seven-year lead time for orders

1998 February 8
100 weeks to Y2K. Many failures already reported

1999 January
One-year projections fail; insurance for Y2K-related losses and liability becomes popular

January 1
Last year of the 1900s begins; "99" might be a signal Transition to the Euro begins.

March
Securities Industry Association simulates December 29, 1999, trading

April 1
New York state's, Canadian, Japanese, and U.K. fiscal year (FY) 2000 starts

April 20
255 days left to year 2000

July
Six-month projections fail

July 1
FY 2000 begins in 46 U.S. states

August 22
Global Positioning System (GPS) rolls over from week 1024 to week 0001

September 1
FY 2000 begins in the state of Texas

September 9
9/9/99 often used as default "nonsense" date

September 23
99 days to year 2000

October
Three-month projections fail

October 1
FY 2000 starts in Alabama, Michigan, and the U.S. federal government

October 3
90-day projections fail

December
One-month projections fail; electrical generators sell out; hoarding begins

December 2
30-day projections fail

December 31
Sometimes used as "Never Expires" date (IBM tapes are marked 99365 - all could expire today. Blue Friday: Largest one-day sell-off in stock market history; long lines at ATM machines; support for much software might cease after today, 1999/99/99 a really "nonsense" date

2000 January 1, Black Saturday
Computer passwords expire, locking administrators out of system; noncompliant systems (fire alarms, heating systems, power grids, telephone routing and billing, medical care, military, air traffic, Internet, and financial exchanges) fail; incorrect bills are send out; manual paperwork begins; unemployment drops; supply chains begin disruption; first casualties occur; litigation begins. Still twentieth century and second millennium.

January 3, Monday
First business day of the year 2000 in the U.S.

January 4, Tuesday
First business day of the year 2000 in the U.K.

January 8, Saturday
The first "We Survived" party is held

February 1
The second "We Survived" party is held

February 29, Tuesday
Some major software packages do not think this date exists. Some say that some PDP-11 computers will not boot after this date.

March 1
Some leap-year errors might not have appeared yesterday

2001 January 1
Third millennium and twenty-first century start

February 29
Will not exist

2002
Transition to the Euro is completed within contiguous Europe

January 1
Burroughs Unisys A Series system date fails

2005
Some really old versions of UNIX (e.g., 16 bit BSD) die this year

2009
FAA finishes its Year-2000 preparations (U.S.)

2020 January 1
Systems still using 1920 as a pivot year fail Macintosh (System 6.0.4+) Date & Time Control Panel can no longer set the current date

2023 December 23, Sunday
End of the world, according to Mayan calendar

2030 January 1
Systems still using 1930 as pivot year fail

2036 January 1
Burroughs Unisys A Series system date fails

February 6
2**32 seconds from January 1, 1900

2038 January 19
UNIX: 2**31 seconds from January 1, 1970

2040 February 6
At 06:28:16, old Macs' longword seconds from January 1, 1904, overflow

2042 September 17
IBM 370 TOD clock overflows

2044 January 1
MS-DOS: 2**6 years from 1980, setting the most significant bit (MSB). Signed variables using this get a negative date

2046 January 1
Amiga system date failure

June 8
Some UNIX password aging fails; 64*2 weeks from 1970

2049 December 31
Microsoft Project 95 limit

2078 December 31
Excel 7.0: The Last Day

2079 June 6
2**16 days from January 1, 1900

2080 January 1
MS-DOS file dates, displayed with two-digit years, are now ambiguous

2100 January 1
Y2.1K: most current PC BIOSes run out of dates; MS-DOS DIR renders the file-date years 2100 through 2107 as 99

2106 February 7
UNIX 2**332 seconds from January 1, 1970; time overflows at 06:28:16

2108 January 1
MS-DOS: 2**7 years from 1980; file date overflows

2738 November 28
Approximate day of A.D. 1 million

4338 November 28
COBOL-85 integer day 1,000,000 exceeds six-digit field 9999; HTTP caching fails

10000 January 1
Y10K: four-digit years fail

29602 January 1
Microsoft Windows NT File System (NTFS) fails

29940
New Macs' signed 64-bit time fails (has been OK since 30,081 B.C.)

31086 July 31
Internal Digital Equipment VMS time fails at 02:48:05.47

60056
Win32 64-bit time fails (started from January 1, 1601)

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Thu Oct 1 20:48:51 MET DST 1998 Wolfgang Braun