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Toffolo signed for Huddersfield Town on 17 January 2020 on a two-and-a-half-year deal.

On 29 January 2018, Toffolo signed for Championship club Millwall on a deal until the end of the Season. He was released by Millwall at the end of the 2017–18 season without playing a game.

On 12 June 2018, Toffolo signed for League Two club Lincoln City on a two-year deal. He played every one of Lincoln's 46 games that season and won a place in the PFA League Two team of the year.

After missing out one game, due to illness, Toffolo scored on his return to the first team, in a 3–2 win over Bury on 7 January 2017. His handful of first team appearances lead the club keen on extending his loan spell until the end of the season; which was confirmed on 8 January 2017. However, he was then sent–off for a second bookable offence, in a 1–1 draw against Sheffield United on 18 February 2017. After missing out three matches, Toffolo then scored again on 11 March 2017, in a 3–2 loss against Gillingham. Towards the end of the 2016–17 season, Toffolo soon lost his first team place after Townsend managed to regain his first team place in the left–back position. At the end of the 2016–17 season, Toffolo went on to make 22 appearances and scoring two times in all competitions.

Despite suffering from a muscle strain whilst on Norwich City's pre–season tour, Toffolo joined Doncaster Rovers of League One on loan from 31 August 2017 until 3 January 2018.

Toffolo made his first appearance in a 1–0 defeat at Northampton Town, being subbed at half time by James Coppinger as Doncaster had fallen behind and changed formation. However, he started out on the substitute bench, due to fitness concerns as well as, competition from Danny Andrew and Craig Alcock for the left–back position. Soon afterwards, he established himself in the starting eleven following Andrews' injury. He then had a handful of first team appearances until he suffered a foot injury following a 1–0 loss against Oxford United on 9 December 2017. As a result, his loan spell at the club ended shortly afterwards and by the time of his departure Toffolo had made 17 appearances for Doncaster Rovers.

He started the 2016–17 season, appearing in a 6–1 win over Peterborough United on 30 August 2016, assisting two times in the EFL Trophy. After his loan spell at Scunthorpe United finished at the end of the 2016–17 season, Toffolo had his contract activated after Norwich City opted to take up their option of a contract extension to ensure his stay for the 2017–18 season.

On 21 January 2016, Toffolo joined League One side Peterborough United on loan until the end of the season.

Toffolo made his Scunthorpe United debut, coming on as a late substitute, in a 4–0 win over Southend United. Since making his debut, he started for the next seven matches in the left–back position until he suffered an injury. After returning from injury, Toffolo found himself in a competition with Conor Townsend over a left–back position. Following Townsend's own injury, Toffolo returned to the first team on 17 December 2016, starting the whole game, in a 3–0 win over Millwall.

In August 2016, his girlfriend Annie Bell gave birth to the couple's first child, a boy named Luca Stefano.

After his loan spell at Swindon Town ended, Toffolo had his contract activated after Norwich City opted to take up their option of a contract extension to ensure his stay for the 2015–16 season. Following this, he said that he was determined to stay at the club to fight for his first team place there. He was then featured in the club's pre–season tour in number of matches. On 25 August 2015, he made his first-team debut for Norwich, playing the full 90 minutes, in the League Cup second round 2–1 victory away to Rotherham United, aged 20 years and 6 days. After the match, his performance was praised by Manager Alex Neil. Soon after, Toffolo signed a two–year contract extension with the club.

During his time at the club, Toffolo established himself as a fans favourite at Swindon and this resulted in the Swindon Town Supporters Trust deciding to fund his loan in January 2015. He also hit the headlines for his engagement with the local community in Swindon and has been involved in a number of charitable events and school visits over and above the usual club player appearance commitments. He is also an Ambassador for Dementia UK (his grandfather having suffered from the condition).

On 19 October 2015, he joined Championship side Rotherham United on a one-month loan.

He made his Championship debut the next day on 20 October 2015 in a home game against Reading which finished 1–1. On 23 November 2015, his loan was extended to January 2016. He appeared in every match since joining the club on loan, establishing himself in the left–back position. However, he suffered a virus and it kept him out for a month before returning to his parent club in January 2016. By the time of his departure, he made seven appearances for the side.

In March 2015, Toffolo was called up for the England U20 squad for the first time. His U20 debut was in a friendly against the United States on 29 March 2015, at Home Park, which England won 2–1. Harry was selected as part of the 23 man squad to play in the Mercedes Benz Cup Tournament in October 2015. He played the full 90 minutes of the 3–1 victory against the Netherlands and came off the bench on 63 minutes and assisted the winning goal in the 2–1 victory against Turkey. He again played the full 90 minutes in the final game, a 1–0 defeat against the hosts, Germany.

In the 2014–15 season, Toffolo was an unused substitute in the League Cup for Norwich City against Crawley Town in the Second round on 26 August 2014. and Shrewsbury Town in the Third round on 23 September.

On 20 October 2014, Toffolo joined Swindon Town on loan for one month.

He made his debut as a substitute for Swindon Town in the 2–2 draw at home to Colchester United and his first start in the 1–0 win at Home to Preston North End on 4 November 2014. Toffolo quickly established himself in the first team at Swindon Town, playing in the left-wing back position. As a result, Toffolo's loan spell with Swindon Town was extended until the end of the season. Since making his debut for the club, he started in every matches until he suffered a medial ligament injury that saw him missed two matches.

After returning to the first team for a match against Walsall as a substitute on 26 December 2014, Toffolo then regained his first team place at the club since coming back from injury to help the side challenge their hopes for promotion. He scored his first league goal in a 3–0 win at home against Notts County on 7 March 2015 and has provided regular assists. Towards the end of the season, Toffolo suffered injuries on two occasions. After missing out in both legs of the play–offs, he made his return in the play-offs final against Preston North End, where he started before being substituted in the 66th minutes, in a 4–0. After this, Toffolo went on to make a total of 30 appearances and scoring once in all competitions.

In 2013, Toffolo played for them in the 2013 FA Youth Cup, as Norwich beat Chelsea 4–2 on aggregate in the final. During the tournament, he scored twice in the last 16 of the FA Youth Cup, in a 2–1 win over Millwall's Under-18 on 31 January 2013. After this, Toffolo signed his first professional contract with the club.

Toffolo made his Peterborough United debut two days after signing the club, starting the whole game, in a 2–1 loss against Gillingham. Since making his Peterborough United debut, Toffolo became a first team regular for the next four matches. However, his time at Peterborough United suffered a setback, due to injuries and international commitment. Despite making one more appearance, Toffolo finished the 2015–16 season, making 7 appearances for the side.

In late–February 2013, Toffolo was called up by England U18 side for the first time. He made his debut starting for England U18s in a friendly against Belgium U18 on 15 March 2013 at the age of 17 years, 6 months and 14 days, in which they lost 1–0. This turns out to be his only appearance for England U18.

Later in 2013, Toffolo was called up by U19 side for the first time. On 5 September 2013, he made his debut for the England U19s in a friendly against Estonia U19, where they won 6–1. He then went on to play in a UEFA Qualifying Tournament in Slovenia, playing in the matches against Slovenia U19 and Switzerland U19, as England finished as group winners.

Toffolo was born in Welwyn Garden City, Hertfordshire, and grew up in Watton-at-Stone where he supported Chelsea. He joined Norwich City in 2008 as an under-14 player. Three years after joining the club, Toffolo joined the Academy in March 2011. Later that year, he earned his first scholarships with the club.

Harry Stefano Toffolo (born 19 August 1995) is an English professional footballer who plays as a left-back for Championship club Huddersfield Town.