| Event | Year | Start | End | Races | Teams |
|---|---|---|---|---|---|
| Winter Invitation Weekend | 1999 | 20 Nov | 20 Nov | 6 | 9 |
| Pumpkin Patch Regatta | 1999 | 23 Oct | 24 Oct | ||
| Carl Miller Regatta | 1999 | 02 Oct | 03 Oct | ||
| East Coast Championship | 1999 | 24 Sep | 26 Sep | 7 | 26 |
| Inofficiellt Svenskt Mästerskap & Stockholms DM | 1999 | 18 Sep | 19 Sep | 6 | 8 |
| Fleet 4 Championship | 1999 | 11 Sep | 12 Sep | 8 | 8 |
| Mid-Atlantic Championship | 1999 | 11 Sep | 12 Sep | 3 | 13 |
| UK National Championship & European Cup | 1999 | 09 Sep | 12 Sep | 7 | 50 |
| Deutsche Meisterschaft | 1999 | 28 Aug | 04 Sep | 5 | 40 |
| Canadian Olympic Regatta | 1999 | 26 Aug | 29 Aug | 8 | 20 |
| Weymouth Open | 1999 | 21 Aug | 22 Aug | 6 | 20 |
| Oak Harbour Regatta | 1999 | 14 Aug | 14 Aug | 5 | 7 |
| Fishing Bay Annual | 1999 | 14 Aug | 15 Aug | ||
| Kingston No Frills Regatta | 1999 | 07 Aug | 08 Aug | 10 | 7 |
| Abersoch Open | 1999 | 06 Aug | 08 Aug | 3 | 11 |
| Dansk Mesterskab | 1999 | 01 Aug | 01 Aug | 6 | 15 |
| Hyannis Annual | 1999 | 30 Jul | 01 Aug | 6 | 11 |
| New England Championship | 1999 | 17 Jul | 18 Jul | 6 | 15 |
| Ontario Championship | 1999 | 17 Jul | 18 Jul | 9 | 8 |
| World Championship | 1999 | 04 Jul | 10 Jul | 5 | 157 |
| Hampton Annual | 1999 | 03 Jul | 04 Jul | ||
| Eastern Canadian Championship | 1999 | 02 Jul | 04 Jul | 7 | 13 |
| Pre-Worlds | 1999 | 02 Jul | 04 Jul | 4 | 88 |
| South Bay Regatta | 1999 | 01 Jul | 01 Jul | 6 | 7 |
| Euro Cup – Nieuwpoort | 1999 | 25 Jun | 27 Jun | 9 | 16 |
| Nepean One Design | 1999 | 19 Jun | 20 Jun | 7 | 8 |
| Short Course Championship | 1999 | 12 Jun | 13 Jun | 6 | 20 |
| Canadian Championship | 1999 | 11 Jun | 13 Jun | 5 | 18 |
| One Day Open Meeting | 1999 | 06 Jun | 06 Jun | 4 | 11 |
| Québec Championship | 1999 | 05 Jun | 06 Jun | 7 | 9 |
| Scandinavian Championship & Euro Cup | 1999 | 04 Jun | 06 Jun | 6 | 20 |
| North American Championship | 1999 | 31 May | 04 Jun | 7 | 14 |
| Bristol Spring | 1999 | 22 May | 23 May | 7 | 6 |
| Pfingstbush | 1999 | 22 May | 24 May | 6 | 30 |
| Pfingstwettfahrten | 1999 | 22 May | 24 May | 2 | 15 |
| Eck-Days | 1999 | 15 May | 16 May | 5 | 33 |
| Hampton Trapeze | 1999 | 15 May | 16 May | 5 | 6 |
| Hoover Spring Regatta | 1999 | 15 May | 16 May | 10 | 7 |
| Euro Cup – Riva del Garda | 1999 | 13 May | 16 May | 5 | 49 |
| Grand Prix des Vins de Bordeaux | 1999 | 13 May | 16 May | 10 | 32 |
| No Gas | 1999 | 08 May | 09 May | 5 | 5 |
| Richmond YC Spring Small Boat Invite | 1999 | 08 May | 09 May | 6 | 10 |
| Southern Area Championship | 1999 | 08 May | 09 May | 6 | 36 |
| Wittensee Fight | 1999 | 08 May | 09 May | 4 | 36 |
| Richmond Regatta | 1999 | 01 May | 01 May | 6 | 10 |
| WRSC Spring | 1999 | 01 May | 02 May | 5 | 12 |
| Oak Harbor Spring Free | 1999 | 24 Apr | 25 Apr | 15 | 5 |
| Régional Est | 1999 | 24 Apr | 25 Apr | 3 | 20 |
| Santa Cruz | 1999 | 24 Apr | 25 Apr | 15 | |
| Trapezregatta | 1999 | 24 Apr | 25 Apr | 3 | 29 |
| Inland Championship | 1999 | 17 Apr | 18 Apr | 1 | 40 |
| Hi-Per | 1999 | 10 Apr | 11 Apr | 8 | 6 |
| Easter Regatta Gosford | 1999 | 03 Apr | 04 Apr | 4 | 10 |
| Championnat de France | 1999 | 01 Apr | 04 Apr | 7 | 83 |
| Pre-Spring | 1999 | 27 Mar | 27 Mar | 7 | |
| Championnat du Léman | 1999 | 27 Mar | 28 Mar | 2 | 22 |
| West Coast Midwinters | 1999 | 13 Feb | 14 Feb | 6 | 5 |
| Western Australian State Championship | 1999 | 06 Feb | 14 Feb | 7 | 10 |
| Fish River Dam Regatta | 1999 | 23 Jan | 24 Jan | 3 | 5 |
| Florida Midwinter | 1999 | 08 Jan | 10 Jan | 7 | 15 |
| RYC Midwinters #2 | 1999 | 03 Jan | 03 Jan | 3 | 7 |
| Australian National Championships | 1999 | 01 Jan | 01 Jan |