He also missed this year's Confederations Cup with what he admitted was a "weird" injury (a calcified bone growth in his foot) and has been barely present during this current cycle, playing just five matches of a possible 27.
Sometimes it has been due to need to manage his workload, amid the demands of the Premier League, as a way to keep a healthy relationship between West Ham and New Zealand Football.
But often Reid has been struck down by untimely injuries, a product of the wear and tear from seven years and more than 200 matches for West Ham.
Since the start of the current World Cup cycle Reid has had nine different periods in the casualty ward at West Ham, missing a total of 54 matches.
There has been calf strains, adductor problems, hamstring issues, hip strains, quadriceps injuries and ankle ligament damage.
But he's here now, pronounced fit and well, which is a an almost immeasurable lift for the All Whites. While Chris Wood has arguably taken his mantle as the team's most irreplaceable player - given his current form and the lack of depth at striker - Reid has the biggest impact on the group.
Similar to 2010 captain Ryan Nelsen, Reid makes players around him better by his sheer presence. Aside from his obvious footballing abilities, the 29-year-old adds exponentially to the belief in the group.
He has a quiet public persona, but is a strong presence within the team. The quality of the training sessions improve and his input into team meetings is highly valued, with more than 150 games in the Premier League and duels with Sergio Aguero, Harry Kane and Diego Costa on his CV. He's on a different stratosphere compared to many of his teammates, but relates well to all.
Reid's appearances for New Zealand have been so infrequent recently it's sometimes easy to forget his impact. But it was seen most noticeably on last year's tour of North America, where he was a standout against the USA and Mexico.
He's the fastest defender among the All Whites' back three, the best reader of play and the most comfortable on the ball. He's an experienced organiser and also an attacking threat at set piece, with an impressive vertical leap.
"Winston has a huge impact on the group," said All Whites defender Michael Boxall. "Just having him in camp, being part of the team, it's like everyone's levels go up. It's not just what he brings on the field, but also off it."
The All Whites held their first full training session on Tuesday afternoon at David Farrington Park, before another scheduled practice on Thursday.
Year Appearances All Whites matches
2010 8 8
2011-2014 9 23
2014-2017 5 27