Ryan Wintle

Cardiff City On 23 June 2021, Wintle signed a three-year contract with Cardiff City. He made his Cardiff debut on 7 August 2021, coming on as a second-half substitute for Joe Ralls in a 1–1 draw against Barnsley. He scored his first Cardiff goal in the club's 3–1 win at Wigan Athletic on 8 October 2022. On 4 August 2023, it was announced that Wintle had signed a new three-year deal to keep him at Cardiff until the summer of 2026.

Blackpool (loan) Wintle joined Blackpool on loan on 28 August 2021 for the remainder of the 2021–22 season, making his debut in a 1–0 win over Fulham at Bloomfield Road on 11 September 2021. However, the loan deal had a January 2022 recall option and Wintle returned to Cardiff on 3 January 2022 after playing 18 games for the Seasiders.

Millwall (loan) On 28 August 2024, Wintle joined Cardiff's fellow Championship side Millwall on loan until the end of the season, making his club debut three days later coming on as a second-half substitute in the side's 3–0 league defeat of Sheffield Wednesday at The Den. He scored one Millwall goal, in a 2–2 draw at Sheffield Wednesday on 4 January 2025.

Return to Cardiff City Wintle returned to Cardiff City following the club's 2025 relegation to League One. He joined a squad with many players considerably younger than him (aged 28); he started the side's first home game, against Peterborough United, as the oldest player by five years. He scored the opening goal in Cardiff's 4–0 win over Plymouth Argyle on 30 August 2025, extending the side's unbeaten run at the start of the season to seven games. Wintle was named Cardiff City Player of the Season for the 2025–26 season as the Bluebirds achieved an immediate promotion back to the Championship. Despite this, on 20 May 2026, Cardiff announced the player would be leaving in the summer when his contract expired. Wintle said this was "a decision that was completely out of my control".

Milton Keynes Dons On 13 July 2026, Wintle joined League One club Milton Keynes Dons on a free transfer. He made his debut and scored his first goal for the club in a 4–1 EFL Cup first round defeat away to Norwich City on 8 August 2026.

Career statistics

Honours Cardiff City EFL League One runner-up: 2025–26

Individual Crewe Alexandra Player of the Season: 2019–20 Crewe Alexandra Players' Player of the Season: 2019–20 Cardiff City Player of the Season: 2025–26 Cardiff City Players' Player of the Season: 2025–26