Norwich City 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. 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. 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. 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. 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.
Loan spells Swindon Town (loan) On 20 October 2014, Toffolo joined Swindon Town on loan for one month. He made his debut as a substitute 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. Toffolo quickly established himself in the first team playing in the left-wing back position. As a result, Toffolo's loan spell was extended until the end of the season. After returning to the first team for a match against
Walsall 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. He scored his first league goal in a 3–0 win at home against
Notts County on 7 March 2015. 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, in a 4–0 defeat. Toffolo made a total of 30 appearances and scoring once in all competitions, and provided several assists. 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 was 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).
Rotherham United (loan) On 19 October 2015, he joined
Championship side Rotherham United on a one-month loan. He made his Championship debut the next day in a home game against
Reading which finished 1–1. On 23 November, 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.
Peterborough United (loan) On 21 January 2016, Toffolo joined
League One side
Peterborough United on loan until the end of the season. Toffolo made his debut two days after signing, starting the whole game in a 2–1 loss against
Gillingham.
Scunthorpe United (loan) On the last day of the transfer window, he was loaned to
Scunthorpe United for the rest of the season. The loan deal would kept him until January. Toffolo made his 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. Toffolo scored his first goal in a 3–2 win over
Bury on 7 January 2017. Scunthorpe extended his loan spell until the end of the season the following day. He was then sent–off for a second bookable offence in a 1–1 draw against
Sheffield United on 18 February. Towards the end of the season, Toffolo lost his first team place after an injury. Throughout the season, Toffolo made 22 appearances and scored twice in all competitions.
Doncaster Rovers (loan) 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.
Millwall 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.
Lincoln City 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.
Huddersfield Town On 17 January 2020, Toffolo signed a two-and-a-half-year contract with
Huddersfield Town for an undisclosed fee. He made his debut the next day in the 0–0 draw against
Brentford.
Nottingham Forest Following Town's defeat in the
2022 EFL Championship play-off final, Toffolo, along with his teammate
Lewis O'Brien, moved to
Premier League side
Nottingham Forest, who defeated Town in the aforementioned final. Toffolo scored his first Nottingham Forest and top-flight goal on 9 December 2023 against Wolverhampton Wanderers. On 1 January 2024, Forest announced that they had exercised a one-year extension option in Toffolo's contract to keep him at the
City Ground until the summer of 2025. In June 2025 it was announced that Nottingham Forest had released Toffolo. ==International career==