| Key Dates For The 1999-2000 NBA Season |
| Day | Date | Event |
| Sun. | Aug. 1 | Teams may begin signing player contracts |
| Sun. | Sept. 23-26 | League Meetings
(Vancouver, British Columbia) |
| Fri. | Oct. 1 | Basketball Hall of Fame Induction Ceremonies |
| Tues. | Oct. 5 | Opening Day of Training Camp |
| Mon. | Oct. 11 | Miami Heat vs. Maccabi Tel Aviv (Tel Aviv, Israel) |
| Thurs. | Oct. 14-16 | McDonald's Championship
International club champions, including San Antonio Spurs (Fila Forum; Milan, Italy) |
| Fri. | Oct. 29 | Last Day of Pre-Season |
| Fri. | Oct. 29 | Board of Governors Meeting (New York, NY) |
| Mon. | Nov. 1 | Rosters set for opening day (6 p.m. ET) |
| Tues. | Nov. 2 | 1999-00 NBA Regular Season begins |
| Sat. | Nov. 6-7 | 1999 NBA Japan Games
Sacramento Kings vs. Minnesota Timberwolves (Tokyo Dome; Tokyo, Japan) |
| Wed. | Jan. 5 | 10-day contracts may now be signed |
| Mon. | Jan. 10 | All player contracts guaranteed for full season |
| Fri. | Feb. 11-13 | All-Star 2000 (Oakland, CA) |
| Thurs. | Feb. 24 | Trading Deadline (6 p.m. ET) |
| Wed. | Apr. 5-8 | Portsmouth Invitational Tournament (Portsmouth, VA) |
| Wed. | Apr. 19 | Last Day of Regular Season |
| Sat. | Apr. 22 | 2000 NBA Playoffs begin |
| Sun. | Mar. 14 | NBA Early Entry eligibility deadline at 11:59 p.m. ET |
| Sun. | Jun. 4 | 2000 NBA Finals earliest possible start date |
| Sun. | Jun. 6 | 2000 NBA Finals latest possible start date |
| Tues. | Jun. 6-12 | NBA Pre-Draft Camp (Moody Bible Institute; Chicago) |
| Wed. | Jun. 21 | 2000 NBA Finals latest possible end date |
| Wed. | Jun. 28 | 2000 NBA Draft (Minneapolis, Minn.) |
| Sat. | Jul. 1 | Teams may begin negotiating, but not sign contracts, with free agents |
| Sat. | Aug. 1 | Teams may begin signing player contracts; salary cap for 2000-01 season established |
| Sept. 15 - Oct. 1 | 2000 Summer Olympic Games (Sydney, Australia) |