An in-depth look into Sutton’s newest recruit: Kai Jennings.
Hailing from Kingston-upon-Thames, just a half-an-hour drive from his new club, Kai Jennings is born and bred in Surrey, and began his footballing journey four miles east with a switch to AFC Wimbledon, crossing the border to South London at the age of six.
He rose through the youth ranks at Plough Lane and quickly became a standout talent in the youth setup, progressing through the various age groups and consistently impressing with his technical ability, vision, and leadership on the pitch.
By his mid-teens, Jennings had established himself as a key player for the Under-16s and later captained the Under-18 side, demonstrating maturity and tactical awareness beyond his years. During his time in the academy, he has been highlighted for his ability to dictate play from midfield, combine effectively with forwards, and contribute goals, with his development at Wimbledon laying the foundation for his senior debut in November 2023 and subsequent loan moves to gain first-team experience.
Indeed, he made his senior debut for Wimbledon in a 5-1 FA Cup victory over Cheltenham Town, coming as a late substitute, before making two further appearances off the bench in EFL Trophy games against Stevenage and Crystal Palace, scoring his first senior goal in the latter.
Jennings has thus trained regularly with Wimbledon’s first team under manager Johnnie Jackson and is viewed as one of the club’s brightest young prospects, and after making the proud step up to the first team, Kai moved on loan to the Isthmian League Premier Division with a switch to Whitehawk midway through the 2023/24 season. He scored three goals in 11 appearances and producing a string of Man of the Match displays which resulted in him rejoining the Sussex side on loan from the start of the 2024/25 season, where he added another three goals across 26 appearances for the Hawks during the first half of the campaign, before seeing his stint back in Sussex come to an end in order to facilitate a move to Walton & Hersham in early 2025.
Jennings impressed in both league and cup competitions under Billy Rowley and scored in their Surrey Senior Cup Final victory over Dorking Wanderers, before earning a move into the National League South in the summer with another loan move, this time to Farnborough, in August 2025.
After appearing a handful of times in pre-season for the Yellows, he has continued to display his composure on the ball and leadership qualities beyond his years, starting in each of his six appearances and has impressed despite their struggles this term under Spencer Day, appearing in draws with Eastbourne Borough and Bath City along with defeats to Dover Athletic, Hemel Hempstead Town, Maidstone United and Salisbury City.
However, his time at the Saunders Transport Community Stadium is set to come to an abrupt end, joining Sutton on loan until the new year as he makes another jump up, this time into the National League, and will add plenty of quality to Chris Agutter’s midfield for the foreseeable future.
