January 12 – Five Iraqi Air Force jets violate the no-fly zone over southern Iraq and two others violate the no-fly zone over northern Iraq. The United States claims that Iraqi aircraft have violated the two no-fly zones a total of 70 times since Operation Desert Fox took place in mid-December 1998.
March 1 – The hot-air balloonBreitling Orbiter 3, with pilots Bertrand Piccard and Brian Jones, begins the first non-stop, round-the-world balloon flight. They will complete the flight on March 19, setting a new distance record for any type of aircraft of 40,804 kilometers (25,360 miles).
Two U.S. Air Force F-15 Eagles intercept two Yugoslav MiG-29s; one of the F-15s shoots down both MiG-29s.
March 27 – After Yugoslav air defense operators find that they can detect U.S. Air Force F-117 Nighthawkstealthattack aircraft using supposedly obsolete Soviet-made radars operating on long wavelengths, the 3rd Battalion of the Yugoslav 250th Missile Brigade shoots down an F-117 with an S-125 Neva/Pechora (NATO reporting name "SA-3 Goa") surface-to-air missile; its pilot ejects and is rescued by search-and-rescue forces near Belgrade. It is the first, and so far the only, time a stealth aircraft has been shot down.
October 11 – Chris Phatswe, a disgruntled and suicidal Air Botswana pilot, commandeers an empty ATR-42 airliner belonging to the airline and circles Sir Seretse Khama International Airport in Gaborone, Botswana, for two hours before crashing his plane into the airline 's other two ATR-42s, which are parked on the ground, killing himself and destroying all three airliners. The incident destroys three of Air Botswana 's four planes and leaves it with no operational aircraft.
November 18 – Trans World Airlines announces a major service expansion in which it adds 46 roundtrip flights per week. The expansion includes new or expanded service to Mexico, the Caribbean, Hawaii, and the Middle East.
Trans World Airlines (TWA) takes delivery from Boeing of its last aircraft bearing the corporate name "Douglas," a McDonnell Douglas MD-83 named Spirit of Long Beach. The delivery brings a symbolic end to TWA's 67-year relationship with Douglas Aircraft, which began with the airline's order of the Douglas DC-1 airliner in 1932 and had continued through the McDonnell Douglas era and after McDonnell Douglas's 1997 merger with Boeing.
December 24 – Five gunmen hijackIndian AirlinesFlight 814, an Airbus A300 with 188 other people on board, over India during a flight from Kathmandu, Nepal, to Delhi, India. The plane lands at Amritsar, India, to refuel, but takes off again without refueling before security forces can immobilize it. It then refuels at Lahore, Pakistan, and flies on to Dubai, where the hijackers release a mortally wounded man they had stabbed and 27 other passengers. The hijackers then force the plane to fly to Kandahar International Airport in Kandahar, Afghanistan, where, after several days of negotiations, they release all the remaining hostages on December 31 in exchange for the release of three senior Islamic fighters held by India.
December 31 – Fear of the Y2K computer bug and possible in-flight consequences for those planes flying during the night of December 31, 1999, and the early morning of January 1, 2000, spreads around the airline industry.
March 1 Hot air balloon Breitling Orbiter 3, with pilots Bertrand Piccard and Brian Jones, begins the first non-stop, round the world balloon flight. This sets a new distance record for any type of aircraft of 40,804 kilometers (25,360 miles).