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Results:
| Winner | Loser | Delta | Comment |
| Nippon | France | :38 | Near penalty for Nippon at start |
| Team Dennis Conner | Prada | 1:07 | 2nd loss for ITA 45 both to Team DC |
| America True | America One | 2:23 | Jib halyard lock failure costs AI |
News from the race course
Winds were in the 18-25 knot range with gusts to 30. Waves were minimal as the course was sheltered by land.
America One was leading America True when their jib halyard lock broke. This damaged their headstay preventing them from hoisting a headsail. This breakdown cost them the race and a who knows how valuable point. Of this Paul Cayard of America One said, "I think the losses are extremely critical and every point is very important. I mean, we don't really know where it's all going to end up."
Team Dennis Conner sailed to a win over Prada. They are the sole team yet to lose. About Stars and Stripes navigator Peter Isler says, "We had some new generation sails out there that were certainly not slowing us down at all. We've made some subtle changes to the boat, both above and below the waterline, and the crew is sailing well."
Nippon got back up from a loss and gained their first semifinal point. From the French team Le Defi, Luc Gellseau made a sarcastic comment about the umpires, "We learned today that when you are in 25 knots, when you are on starboard [right-of-way boat], you have to keep clear of a boat on port."
With two flights complete here are the standings
| Team | Won | Loss | Points Back |
| Team Dennis Conner | 2 | 0 | --- |
| America True | 1 | 1 | 1 |
| America One | 1 | 1 | 1 |
| Nippon | 1 | 1 | 1 |
| Prada | 1 | 1 | 1 |
| France | 0 | 2 | 2 |
Flight 3 match ups:
Prada vs. America One
France vs. Team Dennis Conner
America True vs. Nippon
Head to Head Results Standings Table:
| Teams | A1 | AT | FRA | NIP | PRA | TDC |
| A1 | L | W | ||||
| AT | W | L | ||||
| FRA | L | L | ||||
| NIP | W | |||||
| PRA | W | L | ||||
| TDC | W | W |