Loaned in from Millwall in March 2026, Alfie Massey arrived at Southend United with glowing recommendations from those who had overseen his journey through the Lions' academy to the first-team, including former Shrimper Ryan Leonard.

Massey spent time in the academies of West Ham United and Arsenal before progressing through Millwall’s under-18s and under-21s teams. He was part of a Millwall side that reached the FA Youth Cup Semi-Finals in 2023/24.

His debut for the Lions came in an Carabao Cup fixture away at Portsmouth, named in the starting XI for the 1-0 win on the south coast.

In August 2025, Massey joined Wealdstone on loan to build up his senior minutes, making 10 appearances before injury saw him return to his parent club.