Cambridge United Willmott was a product of Cambridge's youth system. He made his senior debut for the club at the age of 17 on 15 September 2007. Willmott was brought on for the last ten minutes at the
Abbey Stadium as Cambridge ran out 2–1 winners against Crawley Town. The winger signed his first professional contract with Cambridge United in December 2007 and went on to score his first senior goal for United in the FA Cup against Boston United at their York Street ground on 25 October 2008, his overall performance deserving of the man of the match award, an award that Cambridge United manager at the time
Gary Brabin concurred with. Willmott featured in Cambridge United's
Conference Premier play-off final defeat to Torquay United at
Wembley Stadium in May 2009. He started in the final and the second leg of the semi-final, a game in which he scored for United. In January 2010, Willmott became an outlandish transfer target for fellow Conference club
Histon but Cambridge United turned their offer down.
Luton Town On signing Willmott, former Luton Town manager Richard Money said "There were a lot of clubs interested in him...I think it's fair to say that most of the bigger clubs in our division were interested in him and one or two clubs as far up as the Championship. We tried to sign him two or three times and it's always nice, with Monday still to come, to get the deal done with some comfort." He made his debut for the
Hatters on 1 February 2011, coming on as a sub in Luton Town's 4–0 victory over Darlington at Kenilworth Road. At the end of the 2010–11 season, Willmott was acclaimed as one of the season's star performers with his inclusion in the Conference team of the season, the only Luton Town player to be represented. As such, he was the subject of transfer speculation in August 2011 when Forest Green Rovers made two bids for him which Luton Town rejected out of hand. After a disappointing 1–1 draw against AFC Telford in December 2011 Willmott, Luton Town's goal scorer, jumped to the defence of under-fire Luton Town manager Gary Brabin when he said "We're all 100 per cent behind the gaffer. We're all working hard in training, we're all committed to the gaffer and we believe he is the man to take us up the league."
Return to Cambridge United Willmott was released by Luton Town at the end of the 2011–12 season and became a free agent. On 17 July 2012, he re-signed with Cambridge United on a two-year contract, less than two years after departing the U's.
Ebbsfleet United On 4 June 2015 Willmott joined Conference South club Ebbsfleet United.
Eastleigh (loan) On 26 November 2015 Willmott joined National League side Eastleigh on a loan until 2 January 2016.
Chelmsford City In July 2016, Willmott signed for
Chelmsford City alongside
Corby Moore, following former manager Rod Stringer to the club. On 16 August 2016, Willmott made his debut against
Truro City, going on to pick up an assist. At the end of the 2016–17 season Willmott collected the Player of the Year award for Chelmsford after contributing over 30 assists in his single season at the club. During his time at Chelmsford, Willmott worked in a local supermarket alongside playing for the club.
Return to Newport County On 18 May 2017, Willmott re-joined Newport County on a two-year contract. He made his second debut for Newport on the opening day of the 2017–18 season, in a 3–3 draw at
Stevenage. Whilst at Newport, Willmott lived with teammates including
Joss Labadie across the road from Newport's ground,
Rodney Parade. On 27 January 2018 Willmott assisted the goal for
Pádraig Amond in the 1–1 FA Cup 4th Round draw against
Premier League club
Tottenham Hotspur. Tottenham won the replay 2–0. On 6 January 2019, Willmott assisted the first goal for
Jamille Matt in the 2–1 FA Cup 3rd Round win against
Premier League club
Leicester City. On 5 February 2019 Willmott scored the first goal and assisted the second goal for Pádraig Amond in the 2–0 FA Cup 4th Round replay win against Championship club
Middlesbrough. On 8 February 2019 he signed a two-year contract extension to the end of the 2020–21 season. In the FA Cup 5th round on 16 February 2019 Willmott provided the assist for Amond's goal in Newport's 4–1 defeat against reigning Premier League champions
Manchester City. Willmott was part of the team that reached the
League Two playoff final at
Wembley Stadium on 25 May 2019. Newport lost to
Tranmere Rovers, 1-0 after a goal in the 119th minute. In June 2021 Willmott signed a one-year contract extension with Newport County to the end of the 2021-22 season. In March 2022 he extended his contract until the end of the 2022-23 season. He was released by Newport at the end of the 2022-23 season.
Exeter City (loan) On 1 February 2021, Willmott joined
League Two side
Exeter City on loan for the remainder of the 2020-21 season. He made his debut for Exeter as a second-half substitute in the 1-0 League Two win against Stevenage on 2 February 2021. He made his home debut for Exeter in the starting line-up for the 3-2 League Two win against Bradford City on 6 February 2021, providing the assist for Exeter's second goal. He scored his first Exeter goal in the 2-1 League Two win against Colchester United on 23 February 2021.
Walsall (loan) On 5 January 2023, Willmott joined fellow League Two club
Walsall on loan until the end of the
2022–23 season.
Woking On 16 June 2023 Willmott joined
National League club
Woking on a permanent contract. On 20 October 2023, Willmott joined
National League South side,
Weston-super-Mare on loan for the remainder of the season. On 26 April 2024, it was announced that Willmott would leave Woking at the end of his contract in June.
Barry Town United On 1 August 2024, Willmott joined
Cymru Premier club
Barry Town United. == International career ==