The defender injured an ankle in a West Ham training session and will miss the playoff matches as well as West Ham's clash with Norwich this weekend. He travelled immediately to see a specialist in Holland to discover the full extent of the damage. Scans revealed he will be out of action for the next few weeks.
It is a massive blow to the New Zealand side.
They were already huge underdogs for next Thursday's match, but Reid was the one player that they could not afford to lose.
He has been in brilliant form for the Hammers, his value shown by the fact the London club were prepared to fork out over 100,000 pounds (NZ$192,000) for a private jet to ensure he could play for the club on Saturday against Norwich and then fly to Los Angeles in time for the All Whites training camp.
Reid's displays at the heart of defence this season have even caught the eye of Arsenal manager Arsene Wenger, and he has emerged as a likely target of the club, with one report claiming the Gunners are preparing a $12 million bid.
Reid is the one All White playing at the highest level every week and would have been the key to the 90 minute defensive effort required in Mexico City next week.
Though still relatively inexperienced at international level (he made his debut in 2010), the 25-year-old has also matured into a strong leader, and is starting to show some of the qualities that made Ryan Nelsen such a great captain.
Reid's absence leaves a massive hole. Ben Sigmund is a solid player but was badly exposed in previous matches against Mexico while Ivan Vicelich is 37 and has been earmarked for a defensive midfield role. Andrew Durante is an international rookie and has had a patchy campaign for the Phoenix this season.
All Whites coach Ricki Herbert acknowledged losing his skipper was a blow to the side's preparations for the two-leg intercontinental playoff but his team would remain focussed on the task at hand.
"Losing your captain a week before a match of this magnitude is difficult but this is the nature of football," Herbert said.
"With Winston now sidelined, it presents an opportunity for other players to grasp and we will now move forward with the same levels of determination and commitment our group prides itself on."
"Every player in our squad is relishing the challenge lying ahead and, with or without Winston, the end goal remains the same."