On 4th July 2013, Norwich City signed England Under-21 winger Nathan Redmond from Birmingham City for £2million, rising to £3.2million depending on appearances etc. This move reunited Redmond with Chris Hughton, Norwich's manager who was previously at Birmingham. Redmond signed a four year contract with Norwich despite interest from Swansea and Everton.

Redmond began his career as a youngster with Birmingham City, his home-town club. He was first noticed by Birmingham City F.C.'s Academy scouts as an eight-year-old while playing alongside older boys, and scored a hat-trick in his first match for the club's under-10 team. He scored three goals as Birmingham's under-15 team reached the semifinal of the Nike Premier Cup for the first time in April 2009, and in the same season played in the club's under-18 Academy side. In the 2009–10 season, despite being still a schoolboy, Redmond made 15 appearances, scoring 3 times, for the Academy under-18s. He also made a few substitute appearances for the reserves.

He was an unused substitute for Birmingham's final home match of the 2009–10 season, aged 16 years and 56 days. Had he taken the field, he would have become the club's youngest first-team player and also the youngest ever Premier League player, at nine days younger than the record set by Fulham's Matthew Briggs in 2007 He made his first-team debut in the Football League Cup second-round tie against Rochdale in August 2010, becoming the club's second-youngest player ever at the age of 16 years and 173 days

To gain first-team experience, Redmond joined League Two club Burton Albion in January 2011 on a month's Football League youth loan. This arrangement allows the player to appear in non-first-team matches for Birmingham when not required by the loaning club. However the loan was cancelled a few days later when the Football League, who had initially ratified the loan, realised that the rules forbade a first-year scholar from signing on loan for a League club. He made two more substitute appearances for Birmingham that season, one in the League Cup and one in the FA Cup, and signed a three-year professional contract as soon as he turned 17, in March 2011

He finished the 2011/12 season with seven goals from 37 appearances in all competitions, and won the club's Young Player of the Year award. The following season, he played 42 games, scoring twice.

Redmond first played for the England under-16 team on 15th October 2009. He made his debut for England under-17s on 3rd August 2010 in the Nordic Tournament in a 5–0 win against Finland under-17s. He played for England in the 2011 FIFA Under-17 World Cup. He made his debut for England's Under-18s in November 2011 against Serbia. In 2013, he was called up to tne England Under-20 squad for the Under-20 World Cup and was also picked for England for the UEFA Under-21 championships, in which he was one of very few players to leave the tournament with any credit (England lost all three games).

Redmond scored the first goal for England's Under-21 side in their 6-0 thrashing of Scotland on 14th August 2013. He made his Norwich debut on 17th August 2013 at home to Everton in the Premier League. The game finished 2-2 and Redmond was named Man of the Match. He scored his first Norwich goal in the 1-0 home win over Southampton on 31st August 2013.

In January 2014, Redmond was reportedly the subject of a transfer enquiry from Swansea City.

He made a total of 39 appearances, scoring once in the 2013/14 season in which Norwich were relegated from the Premier League.

In July 2014, he was linked with Premiership sides Stoke and Southampton with the latter reportedly bidding £9m at the end of August 2014.

Redmond made 47 appearances for Norwich in 2014/15 scoring six goals including one in the play-off semi-final second leg win over Ipswich and one in the 2-0 Championship Play-off final victory over Middlesbrough on 25th May 2015.

Remond made 35 appearances for City in 2015/16, scoring five goals. Following Norwich's relegation to the Championship in May 2016, Redmond was linked with moves to Premiership sides Stoke City, Swansea, Southampton and West Ham.

In May 2016, Redmond played a key role as England's Under-21s won the Toulon tournament for the first time since 1994. Redmond scored goals in a 7-1 win over Guinea U23s and a 4-0 win over Paraguay U23s in the pool stages, as well as setting up Ruben Loftus-Cheek for the Young Lions’ second goal in a 2-1 win over France in the final. Redmond has a total of 29 caps at U21 level, scoring nine goals - only five players have won more U21 caps than Redmond.

On 25th June 2016, Redmond became Norwich's record sale when he joined Southampton for £10m. He signed a five year contract with the Saints. He had played 121 games for Norwich, scoring 13 goals.

Redmond scored on his Southampton debut in a 1-1 home draw with Watford on 13th August 2016.

On 16 March 2017, he was named in the senior England squad that was to play a friendly against Germany and a World Cup qualifying match against Lithuania. He went on to make his full England debut in the Germany match, coming on as a 66th-minute substitute.

In June 2017, Redmond played for England's Under-21s in the European Championships in Poland. He helped the team reach the semi-finals where after a 2-2 draw, they lost on penalties to Germany with Redmond missing the vital kick for England which saw the Young Lions defeated 4-3.

Ahead of Transfer Deadline Day on 1st September 2022, he was linked with a South Coast move to Bournemouth but the deal fell through. The following week he joined Turkish giants Besiktas on 8th September reportedly for £4million.. Besiktas had already signed fellow Englishman Dele Alli on loan from Everton that summer, with former Premier League players Romain Saiss, Gedson Fernandes, Arthur Masuaku and Wout Weghorst in the Black Eagles' squad. Redmond had played 232 times for the Saints, scoring 30 goals.

In his season with Besiktas, he played 25 league appearances, scoring five goals and providing five assists.

In June 2023 Redmond was linked with a Carrow Road return, but isn't understood to be a a player of interest for the Canaries. On 21st July 2023 Redmond signed for Premier League newboys Burnley on a two year deal. He said "I always had aspirations to play again in the Premier League. Burnley's project matches with my ambitions. The management team feel like they can enhance my game more and see the value I can bring on and off the field. It feels like a perfect match." He became Burn;ey's seventh signing of the Summer 2023 transfer window. Unfortunately his first season saw Burnley relegated from the Premier League when they were beaten 2-1 by Tottenham on 11th May 2024.