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| Date | Issue # | Topic |
| M 2 October | 264 | Club Med's Co Skipper |
| TU 3 October | 265 | September Weather America True Out |
| TH 5 October | 266 | Knickerbocker Cup Team Philips Trials |
| F 6 October | 267 | More problems for Team Philips |
| M 9 October | 268 | Columbus Day Edition |
| TU 10 October | 269 | Club Med/BT Challenge |
| F 13 October | 270 | Code 1 Launch Match Race Rankings |
| M 16 October | 271 | BT Challenge/Times Clipper |
| TU 17 October | 272 | Team Adventure BT/Times Clipper |
| TH 19 October | 273 | Farr 40 Trials/ Volvo Ocean Race News |
| F 20 October | 274 | Photo Issue/ Oracle Racing on the water |
| M 23 October | 275 | Bermuda Gold Cup/ KWRW News |
| TU 24 October | 276 | Middle Sea Record/Gold Cup/BT update |
| TH 26 October | 277 | Bermuda Gold Cup/Pace wins tour title |
| F 27 October | 278 | Russell Coutts Injured |
| M 30 October | 279 | Coutts Wins Gold Cup |
| TU 31 October | 280 | Dog Hair Socks/ Calving Resigns |