The 3rd Toronto Film Critics Association Awards, honoring the best in film for 1999, were held on 16 December 1999.^[1]

Winners

• Best Actor:
  • Kevin Spacey – American Beauty

Runner-Up: Jim Carrey – Man on the Moon

• Best Actress:
  • Hilary Swank – Boys Don't Cry

Runner-Up: Cecilia Roth – All About My Mother

• Best Canadian Film:
  • Set Me Fre

Runner-Up: Felicia's Journey

• Best Director:
  • Paul Thomas Anderson – Magnolia

Runners-Up: Sam Mendes – American Beauty and Steven Soderbergh – The Limey

• Best Film:
  • Magnolia

Runner-Up: Being John Malkovich

• Best Screenplay (tie):
  • Being John Malkovich – Charlie Kaufman
  • Magnolia – Paul Thomas Anderson

Runner-Up: American Beauty – Alan Ball

• Clyde Gilmour Award:
  • Elwy Yost