| World Cup – Results (Final) | 1999 | | 6 November |
| World Cup – Results | 1999 |  | 1 October–6 November |
| World Cup – Results (Third place game) | 1999 | | 4 November |
| Formula 1 – Grand Prix – Japanese Grand Prix | 1999 | | 31 October |
| World Cup – Results (Semifinal #2) | 1999 | | 31 October |
| World Cup – Men – Giant slalom – Tignes | 2000 | | 31 October |
| ATP Tour – ATP Masters 1000 – Madrid | 1999 | | 31 October |
| World Cup – Results (Semifinal #1) | 1999 | | 30 October |
| World Cup – Women – Giant slalom – Tignes | 2000 | | 30 October |
| World Cup – Results (Quarterfinal #3) | 1999 | | 24 October |
| World Cup – Results (Quarterfinal #4) | 1999 | | 24 October |
| World Cup – Results (Quarterfinal #1) | 1999 | | 24 October |
| World Cup – Results (Quarterfinal #2) | 1999 | | 23 October |
| World Cup – Results (Playoff) | 1999 | | 20 October |
| World Cup – Results (Playoff) | 1999 | | 20 October |
| World Cup – Results (Playoff) | 1999 | | 20 October |
| Formula 1 – Grand Prix – Malaysian Grand Prix | 1999 | | 17 October |
| European Tour – World Match Play Championship | 1999 | | 17 October |
| UCI World Tour – Giro di Lombardia | 1999 | | 16 October |
| World Cup – Results (Pool A) | 1999 | | 16 October |
| World Cup – Results (Pool C) | 1999 | | 16 October |
| World Cup – Results (Pool D) | 1999 | | 16 October |
| World Cup – Results (Pool B) | 1999 | | 15 October |
| World Cup – Results (Pool A) | 1999 | | 15 October |
| World Cup – Results (Pool E) | 1999 | | 15 October |
| World Cup – Results (Pool D) | 1999 | | 14 October |
| World Cup – Results (Pool E) | 1999 | | 14 October |
| World Cup – Results (Pool B) | 1999 | | 14 October |
| World Cup – Results (Pool C) | 1999 | | 14 October |
| World Rally Championship (WRC) – Rallies – Rally San Remo | 1999 | | 11–13 October |
| World Cup – Results (Pool A) | 1999 | | 10 October |
| World Cup – Results (Pool D) | 1999 | | 10 October |
| World Championships – Men – Road race | 1999 | | 10 October |
| World Cup – Results (Pool E) | 1999 | | 10 October |
| World Cup – Results (Pool B) | 1999 | | 10 October |
| World Championship – Men – Heavyweight | 1999 | | 9 October |
| World Championships – Women – Road race | 1999 | | 9 October |
| World Cup – Results (Pool B) | 1999 | | 9 October |
| World Cup – Results (Pool C) | 1999 | | 9 October |
| World Cup – Results (Pool D) | 1999 | | 9 October |
| World Cup – Results (Pool E) | 1999 | | 9 October |
| World Cup – Results (Pool C) | 1999 | | 8 October |
| World Cup – Results (Pool A) | 1999 | | 8 October |
| World Championships – Men – Time trial | 1999 | | 7 October |
| World Championships – Women – Time trial | 1999 | | 5 October |
| World Cup – Results (Pool E) | 1999 | | 3 October |
| World Cup – Results (Pool D) | 1999 | | 3 October |
| World Cup – Results (Pool B) | 1999 | | 3 October |
| World Cup – Results (Pool A) | 1999 | | 3 October |
| Others – Paris-Tours | 1999 | | 3 October |
| World Cup – Results (Pool C) | 1999 | | 2 October |
| World Cup – Results (Pool A) | 1999 | | 2 October |
| World Cup – Results (Pool E) | 1999 | | 2 October |
| World Cup – Results (Pool B) | 1999 | | 2 October |
| World Cup – Results (Pool D) | 1999 | | 1 October |
| World Cup – Results (Pool C) | 1999 | | 1 October |
Past events
