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Max Jolliffe signed his first professional contract with the U’s in June 2024 and took his first loan spell at Maldon & Tiptree from the Isthmian League North Division in August 2024.
Jolliffe returned to the U’s to begin training with the first-team, in which he eventually picked up his senior professional debut on 15th March 2025 as a late substitute during the 3-0 victory over Fleetwood Town.
During most of the 2025/26 season, Jolliffe undertook multiple loan spells across lower-tier. The first loan spell was with Isthmian League Premier Division club Billericay Town on an initial one-month loan deal on 26th September 2025. One month later, he joined National League club Yeovil Town on loan for the remainder of the 2025/26 season.
His loan spell with Yeovil Town was cut short having made only ten appearances as Joliffe was recalled back to the U’s. His most recent loan spell was at National League team Salisbury where he netted two goals in 16 appearances; he stayed until April 2026. Throughout his various loan spells, he gained valuable first-team experience. After the conclusion of the 2025/26 season, he returned to the U’s with a passion to train alongside the first team at Florence Park and appear in as many matches as he can.