The 1999 Lipton Championships was a tennis tournament played on outdoor hard courts.

Both the men's and women's events took place at the Tennis Center at Crandon Park in Key Biscayne, Florida in the United States from March 15 through March 29, 1999.

The following players received wildcards into the singles main draw: The following players received wildcards into the doubles main draw: The following players received entry from the singles qualifying draw: The following player received entry as a lucky loser: The following players received entry from the doubles qualifying draw: Richard Krajicek defeated Sébastien Grosjean, 4–6, 6–1, 6–2, 7–5 Venus Williams defeated Serena Williams, 6–1, 4–6, 6–4 Wayne Black / Sandon Stolle defeated Boris Becker / Jan-Michael Gambill, 6–1, 6–1 Martina Hingis / Jana Novotná defeated Mary Joe Fernández / Monica Seles, 0–6, 6–4, 7–6(7–1)

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