As skipper of Tokio he looked set to win the W60 class in the 1993–94 Whitbread Round the World Race until the boat was dismasted in the fifth leg.

[6] The year after his Tanner-Tauranga cups double, Dickson won the first of his three ISAF Youth World Championships, with David McKay in the 420 at Perth, Western Australia.

He was beaten that year by the eventual winner Dennis Conner and Stars & Stripes 87 in the Louis Vuitton Cup Final after winning 33 of 34 races in the round-robin phases and sweeping French Kiss 4–0 in the semi-finals.

[8] He resigned his position as CEO of BMW Oracle Racing because of a devastating 1–5 loss in the 2007 Louis Vuitton Cup at the hands of semi-finals opponent Luna Rossa Challenge.

Software billionaire Larry Ellison, the owner of the BMW Oracle team, subsequently officially announced his intentions to launch a challenge for the 33rd America's Cup.

After a two-year absence from racing, Dickson returned to competitive sailing in 2009 as helmsman of Vincitore, finishing 1st in class and 1st overall at the IRC San Francisco Big Boat Series.