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| Date | Issue # | Topic |
| Th 2 December | 101 | Water Level Outlook and Race 1 News and Notes |
| F 3 December | 102 | Fast 2000 dismasted, Playstationon Code Yellow |
| SA 4 December | 103 | Team Adventure enters The Race |
| M 5 December | 104 | Prada makes crucial error Alison wins Osprey Cup |
| Tu 6 December | 105 | 2000 Calendar and Playstation deadline |
| Th 9 December | 106 | Internet portals sponsor Cup teams |
| F 10 December | 107 | America Around the World Projects and the battle for 6th |
| Sa 11 December | 108 | News and Notes from The Race |
| M 13 December | 109 | Playstation will be delivered to England |
| Tu 14 December | 110 | Key West Race Week Outlook |
| Th 16 December | 111 | It's a go for Playstation |
| F 17 December | 112 | Playsatation's attempt ends & Sailing Awards |
| M 20 December | 113 | Two boat testing |
| Tu 21 December | 114 | Kingfisher pictures, Playstation and Cayard |
| Th 23 December | 115 | Christmas Weekend Sailing Weather |
| M 27 December | 116 | Sydney Hobart Record to go |
| Tu 28 December | 117 | Hobart record set |