He is most known for his time as a defender with Premier League club West Ham United and captaining the New Zealand national team.

[3] He was born in North Shore, Auckland, and started playing football at the age of four at local club Takapuna.

In 2004, the then 16-year-old Reid joined the academy of Danish Superliga club FC Midtjylland on a three-year youth contract.

[13] At the same month at aged 17, he made his FC Midtjylland debut in the Royal League tournament against Norwegian side Vålerenga in a 4–0 win.

[29] On 29 September, Reid was sent–off for a straight red card in a 1–0 loss against Akademisk Boldklub in the third round of the Danish Cup.

[44] On 13 May 2010, Reid started in the Danish Cup Final against Nordsjælland, and played 120 minutes after the game went extra time, as FC Midtjylland lost 2–0.

Following his performance at the World Cup, Reid was linked a move away from Midtjylland, with clubs from Europe interested in signing him.

[56] Reid played an important role against Nottingham Forest in the fourth round of the FA Cup, assisting a goal for Victor Obinna, who scored a hat–trick, in a 3–2 win on 30 January 2011.

[59] Once again, however, Reid spent the rest of the 2010–11 season sidelined from the starting eleven, which saw him placed on the substitute bench, as well as, his own injury concern.

[64] Reid suffered a shoulder injury in the first half during a 0–0 draw against Bristol City on 2 November, resulting in him being sidelined for a month.

[76] Reid captained West Ham for the first time in his career against Manchester United in the third round replay of FA Cup and helped the side lose 1–0.

[77] Two months later, he became a stand in captain once again following injuries to Kevin Nolan and Mark Noble, coming against Stoke City and Chelsea.

[83] Reid scored the opening goal in a 3–0 away win against rivals Tottenham Hotspur on 6 October 2013, ending the club's five league match losing streak.

[93] It was announced on 1 March that Reid signed a new six-and-a-half-year contract with West Ham, after much speculation over his future at the club, after being linked with London rivals Arsenal and Tottenham.

[97] In mid–October, Reid suffered a hip injury while on international duty and was sidelined for weeks,[98] making his return on 7 November in a 1–1 draw against Everton.

[102] It was not until on 9 January 2016 when Reid made his return from injury, starting the whole game, in a 1–0 win against Wolverhampton Wanderers in the third round of the FA Cup.

[107] On 10 May, Reid wrote his name into West Ham folklore when he scored the last ever goal at Upton Park in a 3–2 win against Manchester United.

[110] After serving a one match suspension for picking up five yellow cards, he returned to the starting line–up against Tottenham Hotspur on 19 November and set up two goals, but was later–off for second bookable offence, in a 3–2 loss.

[117] In early January 2018, Reid suffered a groin injury,[118] keeping him out until 3 March when he played against Swansea, only to be taken off on a stretcher with an oxygen mask over his face after being knocked unconscious and twisting a knee, resulting in him being substituted in the 27th minute.

[121] Ahead of the 2019–20 season, Reid made his first appearance in a friendly match against SCR Altach and helped them win 3–2 on 11 July 2019.

[124] It was not until on 30 October when he returned from injury, playing 64 minutes for the reserve side, in a 3–2 loss against VfL Wolfsburg II.

[128] Upon joining the club, he said: "The last 19 months hasn't been the easiest time in my career, but hopefully we’ve crossed that bridge now.

[129] In December 2020, Sporting Kansas City announced that they would not be signing Reid on a permanent transfer at the end of his loan and that he would return to West Ham.

[131] On 3 February, Reid made his debut for Brentford in a 3–2 win against Bristol City, coming on late in the game as a substitute.

[133] Reid was hailed as "a giant" by Brentford manager Thomas Frank for helping to get their promotion push back on track following his arrival at the club in February.

[147] On 12 October 2010, Winston picked up his first international red card against Paraguay in Wellington for a "vicious"[148] studs-up tackle on striker Federico Santander in the 90th minute of the All Whites' 2–0 defeat.

[151] Later in the same year on 7 November 2013, Reid was ruled out of the All Whites' FIFA World Cup playoff against Mexico, not only leaving a void on defence, but also with his successor as captain uncertain.

[160] Reid made his first national side appearance in two years, coming against Republic of Ireland, where he captained and played 45 minutes before being substituted, as they lost 3–1.

[8] In July 2015, Reid became a first time father when his wife, Yana, gave birth to twins, Ariana and Damien.

[164] In August 2015, Reid launched a footballing scholarship at Scots College, which were won by Sarpreet Singh and Max Mata.