May 9 - The Taliban movement says that its forces have retaken the key central town of Bamyan from the opposition alliance.
June
June 20 - The Red Cross pulls non-essential foreign staff out of Afghanistan after 10 of its workers were beaten.
July
July 6 - U.S. President Bill Clinton imposes financial and commercial sanctions on Afghanistan's ruling Taliban movement because of its support of Saudi terrorism suspect Osama Bin Laden.
July 19 - The Six plus Two Group on Afghanistan adopted the Tashkent Declaration, in which the members pledged not to provide arms to any party in the Afghan conflict and not to allow the use of their territory for such purpose.
July 28 - Thousands of Taliban fighters launch an offensive to crush Ahmad Shah Masood, the last hurdle between the Islamic militia and control of the whole of Afghanistan. This July Offensive was condemned in an October Presidential Statement of the UN Security Council. The UN Secretary General specifically pointed out that the offensive was reinforced by thousands of recruits from religious schools in Pakistan.
August
August 1 - Taliban fighters seize opposition leaderAhmad Shah Masood's key Bagram airbase in an offensive to establish total dominance of Afghanistan; anti-Taliban fighters recapture the airbase on August 5.
September 1 - Afghan Health Minister Mulla Mohammad Abbas Akhund met with Pakistani Health Minister Javed Hashmi and Pakistani Director of General Health Ghayur Ayub to discuss the lack of medical facilities in Afghanistan.
September 2 - The Afghan Northern Alliance rejected Pakistan's peace efforts and planned to work further with the six-plus-two nations.
Late September - The Taliban issued a decree calling for a one-third reduction in the cultivation of opium over the 1999/2000 season, a 50% reduction of cultivation in some districts in Nangarhar, and a complete ban on cultivation on the lands owned by the Taliban itself. In July 2000, the Taliban would move further, instituting a total opium cultivation ban.
October
October 22 - United States Assistant Secretary of State for South Asia Karl Inderfurth told Congress that the US is “Prepared to work with the Taliban to rid Afghanistan of terrorist networks,” if it would hand over bin Laden to American authorities.
October 29 - Saudi-born terrorism suspect Osama bin Laden is reported to have sought safe passage from the Taliban's Afghanistan to an unknown country.
November
November 14 - UN sanctions against Afghanistan under Resolution 1267 go into force, imposed for not handing over Saudi dissident Osama Bin Laden.