| Race | RS | date | Place Type | Winner | Second | Third | 
| 1005 | 1 | 31 October 1999 | Tignes (FRA) GS255 | Hermann Maier |  AUT | Michael von Grünigen |  SUI | Kjetil André Aamodt |  NOR | 
| Stephan Eberharter |  AUT | 
| 1006 | 2 | 23 November 1999 | Vail (USA) SL293 | Didier Plaschy |  SUI | Thomas Stangassinger |  AUT | Kjetil André Aamodt |  NOR | 
| Matteo Nana |  ITA | 
| 1007 | 3 | 24 November 1999 | Vail (USA) GS256 | Hermann Maier |  AUT | Michael von Grünigen |  SUI | Andreas Schifferer |  AUT | 
| 1008 | 4 | 27 November 1999 | Beaver Creek (USA) DH295 | Hermann Maier |  AUT | Stephan Eberharter |  AUT | Kristian Ghedina |  ITA | 
| 1009 | 5 | 28 November 1999 | Beaver Creek (USA) SG086 | Hermann Maier |  AUT | Stephan Eberharter |  AUT | Lasse Kjus |  NOR | 
| 1010 | 6 | 4 December 1999 | Lake Louise (CAN) DH296 | Hannes Trinkl |  AUT | Hermann Maier |  AUT | Stephan Eberharter |  AUT | 
| 1011 | 7 | 5 December 1999 | Lake Louise (CAN) SG087 | Hermann Maier |  AUT | Fredrik Nyberg |  SWE | Josef Strobl |  AUT | 
| 1012 | 8 | 13 December 1999 | Madonna di Campiglio (ITA) SL294 | Finn Christian Jagge |  NOR | Benjamin Raich |  AUT | Thomas Stangassinger |  AUT | 
| 1013 | 9 | 17 December 1999 | Val Gardena (ITA) DH297 | Kristian Ghedina |  ITA | Josef Strobl |  AUT | Ed Podivinsky |  CAN | 
| 1014 | 10 | 18 December 1999 | Val Gardena (ITA) DH298 | Andreas Schifferer |  AUT | Kristian Ghedina |  ITA | Hermann Maier |  AUT | 
| 1015 | 11 | 19 December 1999 | Alta Badia (ITA) GS257 | Joël Chenal |  FRA | Hermann Maier |  AUT | Rainer Salzgeber |  AUT | 
| 1016 | 12 | 21 December 1999 | Kranjska Gora (SLO) SL295 | Didier Plaschy |  SUI | Benjamin Raich |  AUT | Thomas Stangassinger |  AUT | 
| 1017 | 13 | 22 December 1999 | Saalbach (AUT) GS258 | Christian Mayer |  AUT | Hermann Maier |  AUT | Benjamin Raich |  AUT | 
| 1018 | 14 | 8 January 2000 | Chamonix (FRA) DH299 | Hermann Maier |  AUT | Stephan Eberharter |  AUT | Hannes Trinkl |  AUT | 
| 1019 | 15 | 9 January 2000 | Chamonix (FRA) SL296 | Angelo Weiss |  ITA | Kjetil André Aamodt |  NOR | Matjaž Vrhovnik |  SLO | 
| 1020 | 16 | 9 January 2000 | Chamonix (FRA) KB078 | Kjetil André Aamodt |  NOR | Hermann Maier |  AUT | Paul Accola |  SUI | 
| 1021 | 17 | 15 January 2000 | Wengen (SUI) DH300 | Josef Strobl |  AUT | Hermann Maier |  AUT | Ed Podivinsky |  CAN | 
| 1022 | 18 | 16 January 2000 | Wengen (SUI) SL297 | Kjetil André Aamodt |  NOR | Ole Kristian Furuseth |  NOR | Drago Grubelnik |  SLO | 
| 1023 | 19 | 21 January 2000 | Kitzbühel (AUT) SG088 | Hermann Maier |  AUT | Werner Franz |  AUT | Didier Cuche |  SUI | 
| 1024 | 20 | 22 January 2000 | Kitzbühel (AUT) DH301 | Fritz Strobl |  AUT | Kristian Ghedina |  ITA | 
| Josef Strobl |  AUT | 
| 1025 | 21 | 23 January 2000 | Kitzbühel (AUT) SL298 | Mario Matt |  AUT | Matjaž Vrhovnik |  SLO | Benjamin Raich |  AUT | 
| 1026 | 22 | 23 January 2000 | Kitzbühel (AUT) KB079 | Kjetil André Aamodt |  NOR | Fredrik Nyberg |  SWE | Hermann Maier |  AUT | 
| 1027 | 23 | 29 January 2000 | Garmisch-Partenkirchen (GER) DH302 | Hermann Maier |  AUT | Kristian Ghedina |  ITA | Hannes Trinkl |  AUT | 
| 1028 | 24 | 5 February 2000 | Todtnau (GER) GS259 | Hermann Maier |  AUT | Fredrik Nyberg |  SWE | Michael von Grünigen |  SUI | 
| 1029 | 25 | 6 February 2000 | Todtnau (GER) SL299 | Rainer Schönfelder |  AUT | Kjetil André Aamodt |  NOR | Ole Kristian Furuseth |  NOR | 
| 1030 | 26 | 12 February 2000 | St. Anton am Arlberg (AUT) SG089 | Josef Strobl |  AUT | Didier Cuche |  SUI | Stephan Eberharter |  AUT | 
| 1031 | 27 | 13 February 2000 | St. Anton am Arlberg (AUT) SG090 | Werner Franz |  AUT | |2$Hermann Maier |  AUT | 
| Fritz Strobl |  AUT | 
| 1032 | 28 | 20 February 2000 | Adelboden (SUI) SL300 | Matjaž Vrhovnik |  SLO | Kjetil André Aamodt |  NOR | Mario Matt |  AUT | 
| 1033 | 29 | 26 February 2000 | Yongpyong f**South Korea GS260 | Benjamin Raich |  AUT | Michael von Grünigen |  SUI | Joël Chenal |  FRA | 
| 1034 | 30 | 27 February 2000 | Yongpyong f**South Korea SL301 | Mitja Kunc |  SLO | Ole Kristian Furuseth |  NOR | Mario Matt |  AUT | 
| 1035 | 31 | 3 March 2000 | Kvitfjell (NOR) DH303 | Daron Rahlves |  USA | Didier Cuche |  SUI | Hermann Maier |  AUT | 
| 1036 | 32 | 4 March 2000 | Kvitfjell (NOR) DH304 | Daron Rahlves |  USA | Kristian Ghedina |  ITA | Max Rauffer |  GER | 
| 1037 | 33 | 5 March 2000 | Kvitfjell (NOR) SG091 | Kristian Ghedina |  ITA | Hermann Maier |  AUT | Andreas Schifferer |  AUT | 
| 1038 | 34 | 8 March 2000 | Kranjska Gora (SLO) GS261 | Christian Mayer |  AUT | Joël Chenal |  FRA | Marco Büchel |  LIE | 
| 1039 | 35 | 9 March 2000 | Schladming (AUT) SL302 | Mario Matt |  AUT | Kjetil André Aamodt |  NOR | Thomas Stangassinger |  AUT | 
| 1040 | 36 | 11 March 2000 | Hinterstoder (AUT) GS262 | Christian Mayer |  AUT | Marco Büchel |  LIE | Hermann Maier |  AUT | 
| 1041 | 37 | 15 March 2000 | Bormio (ITA) DH305 | Hannes Trinkl |  AUT | Hermann Maier |  AUT | Christian Greber |  AUT | 
| 1042 | 38 | 16 March 2000 | AUT) SG092 Hermann Maier | Fritz Strobl |  AUT | Werner Franz 
 |  AUT | Andreas Schifferer |  AUT | 
| 1043 | 39 | 18 March 2000 | AUT) SG092 GS263 | Benjamin Raich |  AUT | Christian Mayer |  AUT | Heinz Schilchegger |  AUT | 
| 1044 | 40 | 19 March 2000 | AUT) SG092 SL303 | Ole Kristian Furuseth |  NOR | Benjamin Raich |  AUT | Matjaž Vrhovnik |  SLO |