Pendlebury, 23, started his career coming through the Academy of Berkshire club Reading where he played for 13 years. He made his First-Team debut in January 2021 in an FA Cup tie against Luton Town. At the end of that Season, Olly joined EFL League One side Wycombe Wanderers. He made 4 league appearances scoring 2 while also appearing in cup action and having a short spell with Woking that campaign. At the start of 2022/23, Pendlebury joined Farnborough where he featured regularly before being picked up by National League side Aldershot Town where he was also a regular in their side that campaign. A transfer that summer took Olly up to play in the Scottish Championship for Ayr United where he spent a short time before returning to Hampshire to re-join Farnborough. Once again Olly established himself as a regular in their side taking himself to just shy of 80 appearances for the club across both spells. Now Olly joins The Hawks in the next chapter of his career.