Swansea City Shephard joined
Swansea City from
Cardiff City in the summer of 2011, and progressed through Swansea City's
Academy. Shephard signed his first professional deal with Swansea at the start of the 2013–14 season. Shephard broke into the first-team squad in the first half of the 2014–15 season, and was included on the bench for four
Premier League matches and two cup games. Shephard was rewarded for his progress with a new -year contract until June 2017. On 17 January 2015, Shephard joined
League One team
Yeovil Town on a youth loan deal and made his professional debut three days later against
Preston North End. Yeovil later extended the loan until the end of the season. Shephard went on to make 20 appearances for the Glovers and was awarded Young Player of the Year, as Yeovil were relegated to
League Two. Shephard made his first team debut for Swansea City in the
FA Cup against
Oxford United, on 10 January 2016, in a 3–2 third round defeat. On 24 March 2016, Shephard returned to Yeovil Town on a month loan deal. Initially brought in as cover for fellow Swansea loanee
Connor Roberts, Shephard started six matches all in a defensive midfield role as he helped Yeovil to avoid relegation. On 1 July 2016, Shephard joined Yeovil Town for a third time on a six-month loan deal. Upon his return from his loan spell with Yeovil, Shephard was released by Swansea at the end of the 2016–17 season.
Peterborough United On 10 July 2017, Shephard signed for
League One club
Peterborough United on a two-year contract.
Forest Green Rovers On 28 June 2018, Shephard joined
League Two club
Forest Green Rovers for an undisclosed fee on a two-year contract. Shephard was released by Forest Green Rovers at the end of the 2019–20 season.
Newport County On 2 September 2020 Shephard joined Newport County on a one-year contract. He made his debut for Newport on 5 September 2020 in the 2–0
EFL Cup win against Swansea City. He scored his first goal for Newport on 19 September 2020 in the League Two 2–1 win against Barrow. Shephard played for Newport in the
League Two playoff final at
Wembley Stadium on 31 May 2021 which Newport lost to
Morecambe, 1–0 after a 107th-minute penalty.
Salford City In June 2021 Shephard rejected a contract extension at Newport and signed a two-year contract at Salford City. In June 2023 Shephard extended his Salford contract until the end of the 2024–25 season. On 12 May 2025, the club announced he would be released in June when his contract expired.
Newport County On 6 August 2025 Shephard rejoined Newport County on a one year contract. He made his second debut for Newport on 9 August 2025 in the 2-1 League Two win against Crawley Town, scoring Newport's second goal. ==International career==