The 1999 Big South Conference men's basketball tournament took place February 25–27, 1999, at the Asheville Civic Center in Asheville, North Carolina. For the first time in their school history, the Winthrop Eagles won the tournament, led by head coach Gregg Marshall.
Format
All six teams participated in the tournament, hosted at the Asheville Civic Center. Teams were seeded by conference winning percentage. Elon and High Point were making their transition to the league during the season, and were not yet included as full members.