Oliver Callaby joined Skegness Town ahead of the 2026/27 season as a young player looking to continue his development in the men's game. A dual-signed member of Boston United's Youth Team, Ollie has already gained valuable senior experience at Step 6 with Louth Town and Pinchbeck United, helping him adapt to the demands of non-league football at an early stage.

Primarily a right-sided midfielder, Ollie is equally comfortable operating at right-back, offering versatility and energy down the flank. Blessed with a strong work ethic and a willingness to learn, he is a good prospect with the attitude and desire to continue progressing as part of the Lilywhites squad.

July 2026

Sat, 25 July

Hucknall Town FC

Skegness Town FC

GCE Hire Fleet United Counties Football League 26 - 27 - Premier Division North

Sub On (90’)

August 2026

Sat, 01 August

Skegness Town FC

Hinckley AFC

GCE Hire Fleet United Counties Football League 26 - 27 - Premier Division North

Sub On (90’+2)