In 2013, Toffolo played for them in the 2013FA Youth Cup, as Norwich beatChelsea 4–2 on aggregate in the final.[8] During the tournament, he scored twice in the last 16 of the FA Youth Cup, in a 2–1 win overMillwall's Under-18 on 31 January 2013.[9] After this, Toffolo signed his first professional contract with the club.[10]
In the 2014–15 season, Toffolo was an unused substitute in theLeague Cup for Norwich City againstCrawley Town in the Second round on 26 August 2014.[11] andShrewsbury Town in the Third round on 23 September.[12]
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.[13] Following this, he said that he was determined to stay at the club to fight for his first team place there.[14] He was then featured in the club's pre–season tour in number of matches.[15] 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 toRotherham United, aged 20 years and 6 days.[16] After the match, his performance was praised by Manager Alex Neil.[17] Soon after, Toffolo signed a two–year contract extension with the club.[18]
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.[19] 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.[20]
On 20 October 2014, Toffolo joined Swindon Town on loan for one month.[21] He made his debut as a substitute in the 2–2 draw at home toColchester United,[22] and his first start in the 1–0 win at Home toPreston North End on 4 November.[23] Toffolo quickly established himself in the first team playing in the left-wing back position.[24] As a result, Toffolo's loan spell was extended until the end of the season.[25]
After returning to the first team for a match againstWalsall as a substitute on 26 December, Toffolo then regained his first team place at the club since coming back from injury to help the side challenge their hopes for promotion.[26] He scored his first league goal in a 3–0 win at home againstNotts County on 7 March 2015.[27] After missing out inboth legs of the play–offs,[28] he made his return in theplay-offs final againstPreston North End, where he started, in a 4–0 defeat.[29] Toffolo made a total of 30 appearances and scoring once in all competitions, and provided several assists.[30]
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.[31] He also hit the headlines for his engagement with the local community in Swindon,[32][33] and was involved in a number of charitable events and school visits over and above the usual club player appearance commitments.[34] He is also an Ambassador forDementia UK (his grandfather having suffered from the condition).[35]
On 19 October 2015, he joinedChampionship side Rotherham United on a one-month loan.[36] He made his Championship debut the next day in a home game againstReading which finished 1–1.[37] On 23 November, his loan was extended to January 2016.[38] He appeared in every match since joining the club on loan, establishing himself in the left–back position.[39] However, he suffered a virus and it kept him out for a month before returning to his parent club in January 2016.[40] By the time of his departure, he made seven appearances for the side.
On 21 January 2016, Toffolo joinedLeague One sidePeterborough United on loan until the end of the season.[41] Toffolo made his debut two days after signing, starting the whole game in a 2–1 loss againstGillingham.[42][43]
On the last day of the transfer window, he was loaned toScunthorpe United for the rest of the season.[44] The loan deal would kept him until January.[45] Toffolo made his debut coming on as a late substitute in a 4–0 win overSouthend United.[46] Since making his debut, he started for the next seven matches in the left–back position.[47] Toffolo scored his first goal in a 3–2 win overBury on 7 January 2017.[48] Scunthorpe extended his loan spell until the end of the season the following day.[49] He was then sent–off for a second bookable offence in a 1–1 draw againstSheffield United on 18 February.[50] Towards the end of the season, Toffolo lost his first team place after an injury.[51] Throughout the season, Toffolo made 22 appearances and scored twice in all competitions.
Despite suffering from a muscle strain whilst on Norwich City's pre–season tour, Toffolo joinedDoncaster Rovers ofLeague One on loan from 31 August 2017 until 3 January 2018.[52] Toffolo made his first appearance in a 1–0 defeat atNorthampton Town, being subbed at half time byJames Coppinger as Doncaster had fallen behind and changed formation.[53] However, he started out on the substitute bench, due to fitness concerns as well as, competition fromDanny Andrew andCraig Alcock for the left–back position.[54] Soon afterwards, he established himself in the starting eleven.[55]
On 29 January 2018, Toffolo signed for Championship club Millwall on a deal until the end of the season.[56] He was released by Millwall at the end of the 2017–18 season without playing a game.[57]
On 12 June 2018, Toffolo signed forLeague Two clubLincoln City on a two-year deal.[58] He played every one of Lincoln's 46 games that season and won a place in the PFA League Two team of the year.[59]
On 17 January 2020, Toffolo signed a two-and-a-half-year contract withHuddersfield Town for an undisclosed fee.[60] He made his debut the next day in the 0–0 draw againstBrentford.[61]
Toffolo scored his first Nottingham Forest and top-flight goal on 9 December 2023 against Wolverhampton Wanderers.[63]
On 1 January 2024, Forest announced that they had exercised a one-year extension option in Toffolo's contract to keep him at theCity Ground until the summer of 2025. In June 2025 it was announced that Nottingham Forest had released Toffolo.[63]
In late–February 2013, Toffolo was called up by England U18 side for the first time.[66] He made his debut starting for England U18s in a friendly againstBelgium U18 on 15 March 2013 at the age of 17 years, 6 months and 14 days, in which they lost 1–0.[67] This turns out to be his only appearance for England U18.
Later in 2013, Toffolo was called up byU19 side for the first time.[68] On 5 September 2013, he made his debut for the England U19s in a friendly againstEstonia U19, where they won 6–1.[69] He then went on to play in a UEFA Qualifying Tournament in Slovenia, playing in the matches againstSlovenia U19 andSwitzerland U19, as England finished as group winners.[70]
In March 2015, Toffolo was called up for theEngland U20 squad for the first time.[71] His U20 debut was in a friendly against theUnited States on 29 March 2015, atHome Park, which England won 2–1.[72] Harry was selected as part of the 23 man squad to play in the Mercedes Benz Cup Tournament in October 2015.[73] He played the full 90 minutes of the 3–1 victory against the Netherlands[74] and came off the bench on 63 minutes and assisted the winning goal in the 2–1 victory against Turkey.[75] He again played the full 90 minutes in the final game, a 1–0 defeat against the hosts, Germany.[76]
In August 2016, his girlfriend Annie Bell gave birth to the couple's first child, a boy named Luca Stefano.[77][78]
Toffolo said about his position, quoting: "I love getting forward", he said. "I'm generally a left-back but I like to get forward a lot so the left wing-back role suits me as well. You have to get back and do your job there but I love getting forward and doing as much as I can."[79]
In July 2023, Toffolo was charged by theFootball Association for breaching its betting rules an alleged 375 times between 22 January 2014 and 18 March 2017.[80] On 13 September 2023 it was announced Toffolo had been given a five-month ban by theFootball Association after admitting to the 375 breaches of betting rules. His ban was suspended until the end of 2024–25 and he was also fined £20,956.[81]
^"When Harry Met Sammy".Learn about Swindon Town. Swindon Town Supporters Trust. 5 March 2015. Archived fromthe original on 4 March 2016. Retrieved23 April 2015.
^"International Round Up". Norwich City F.C. 5 September 2013.Archived from the original on 15 January 2018. Retrieved19 January 2018.
^"YOUNG GUNS IN ACTION". Norwich City F.C. 11 October 2013.Archived from the original on 15 January 2018. Retrieved19 January 2018. "INTERNATIONAL ROUND-UP". Norwich City F.C. 16 October 2013.Archived from the original on 15 January 2018. Retrieved19 January 2018.