Early career Drinan began playing football with his local side
Carrigaline United at the age of 4, impressing enough to earn a move to
Cobh Ramblers, where he would play with their Under-19 side for a short time in early 2015 before moving to their rivals
Cork City in the summer of 2015 where he would play until the end of the 2017 season. During his time at Cork's under-19 side, he played alongside
Chiedozie Ogbene,
Cian Coleman and
Conor McCarthy among others.
Cork City Drinan won his first title with
Cork City Under 19's with a win over
Limerick at
Markets Field on 15 December 2015. His first appearance for the first-team came on 9 June 2016, playing 85 minutes of a
friendly against
Fulham. He was part of the side to the Enda McGuill Cup in September 2016, beating
St Patrick's Athletic in the final and qualifying for the
UEFA Youth League in the process. Drinan impressed in the
UEFA Youth League, scoring the winner in a 1–0 win on aggregate against
HJK Helsinki of Finland as well as scoring an equaliser against Italian giants
AS Roma. His first involvement in a first-team squad for a league game was on 23 June 2017 when he was an unused substitute in a 2–1 win over
Derry City at
Maginn Park.
Waterford Drinan dropped down a division to sign for
Waterford of the
League of Ireland First Division in July 2017, making his competitive debut in senior football away to
Cabinteely on 4 August 2017. He scored the first goal of his senior career on 1 September 2017, scoring in a 1–1 draw with
Shelbourne at the
RSC. Drinan finished up the season with 5 appearances and 1 goal to his name as
Waterford won the
League of Ireland First Division, resulting in his first taste of silverware at senior level.
Ipswich Town Drinan began training with English
EFL Championship side
Ipswich Town in October 2017 and was announced as a new signing by manager
Mick McCarthy on 4 January 2018, signing a three-and-a-half-year contract, with the option of an additional one year extension for a fee reported to be £90,000. He was an unused substitute in 4 Championship games and 1
FA Cup game for Ipswich during the 2017–18 season but failed to make his first-team debut as his side finished in 12th place. He impressed his teammates in training during the early months of his time at Ipswich, earning him the nickname "Murph", after former Ipswich and Republic of Ireland striker
Daryl Murphy.
Loans away He joined
National League side
Sutton United on 1 August 2018. He made his debut for Sutton United three days later in a 2–2 draw with
Harrogate Town. He returned to Ipswich in November 2018. On 15 February 2019, it as announced that Drinan had signed for his old club
Waterford on loan until the summer. His loan was a huge success, scoring 7 goals in 18 league games. Drinan signed for Swedish
Superettan side
GAIS on 8 August 2019. He made his debut away to
Dalkurd FF on 18 August 2019. He returned to
Ipswich Town in November at the end of his loan which saw him make 9 appearances for
GAIS. He signed for
Scottish Championship side
Ayr United on loan on 17 January 2020. His debut came the next day in a 1–0
Scottish Cup win over
Ross County to earn a 5th Round tie with
Scottish Premiership side
St Johnstone. He scored his first goal for Ayr on 8 February in a 2–1 loss to
St Johnstone in a Scottish Cup match. He made 9 appearances during his loan spell with Ayr, scoring twice. After years at Ipswich, Drinian made his full senior debut for the club on 5 September 2020 in a 3–0 home win against
Bristol Rovers in the
EFL Cup at
Portman Road, assisting the first goal scored by teammate
Freddie Sears. He made his league debut for the club in a 2–0 win against
Wigan Athletic on the opening day of the 2020–21 league season, although he had to be withdraw at half-time due to a thigh injury, which would rule him out of action for two months. He scored his first goal for the club on 30 January 2021, in a 1–1 draw with
Crewe Alexandra. He made 24 appearances during the 2020–21 season, scoring once.
Leyton Orient On 28 June 2021, Drinan joined
Leyton Orient for an undisclosed fee, signing a two-year deal. On 24 July 2022, Drinan signed a new one-year extension to his existing contract.
Swindon Town On 1 February 2024 he signed for
Swindon Town. He was offered a new contract by Swindon at the end of the 2024–25 season. On 20 June 2025, the club announced he had signed a new two-year deal. Following a strong start to the
2025–26 season for both player and club, Drinan was named
EFL League Two Player of the Month for September 2025 having scored five goals in four matches. He was named League Two Player of the Season at the
EFL end of season awards, also being named in the Team of the Season. ==International career==