Some of the biggest talents in football nearly wore the red and white of Southampton. Here’s a look at some deals that were close but never happened.

2018: James Maddison:

Southampton had a £20m bid accepted for Maddison when he was at Norwich City, but Leicester swooped in with a slightly better offer and convinced him to join. Maddison later admitted: «It was a tough decision, but Leicester felt like the right step for me.»

2020: Ibrahima Sangaré:

Saints were in advanced talks to sign Sangaré for around £9m, with a deal nearly wrapped up before a game against West Brom. However, work permit issues caused the deal to collapse, and PSV stepped in at the last minute to sign him for a reported £7m. He later won the Eredivisie title with them.

2020: Weston McKennie:

McKennie was Southampton’s first choice before the Sangaré attempt, with a £20m deal agreed with Schalke. However, Juventus made a late approach, offering a loan with an obligation to buy for €25m. McKennie later revealed: «It was a dream to play in Serie A, and I couldn’t say no to Juventus.»

2019-2022: Joakim Mæhle:

A long-term target for Saints, Mæhle was on the club’s radar when he was at Genk and later at Atalanta. Despite multiple approaches, a deal never materialized, and he later moved to Atalanta for €10m. In 2021, Southampton tried again, but Atalanta asked for €28m. Now, he plays under former Saints boss Ralph Hasenhüttl at Wolfsburg.

2022: Cody Gakpo:

Southampton made a club-record £32m bid for Gakpo in the summer window, but PSV held out for £35m.

Gakpo later admitted: “I said to myself if I scored once Id go to Southampton, twice i’d go to Leeds, hat-trick i’d stay at PSV. It was in Gods hands now.”

He scored a hat-trick, stayed at PSV and moved to Liverpool 6 months later.

August 2024: Matt O’Riley:

Southampton made an £18m + add-ons offer for O’Riley and were negotiating directly at an owner-to-owner level. However, Brighton outbid them with a £25m package.

August 2024: Justin Bijlow:

Everything seemed set for Bijlow to join Southampton on an initial loan deal with a mandatory purchase clause after 20 appearances. He even said his goodbyes at Feyenoord before flying to England for his medical. However, last-minute concerns over his injury history caused Saints to back out.

August 2024: Liam Delap:

Saints had a £15m + £5m bid accepted by Manchester City, with Russell Martin keen to work with the young striker. However, Delap opted for Ipswich, citing their style of play and first-team assurances as key factors in his decision.

Some of these players could have changed Southampton’s trajectory. Which one do you wish had joined the most?