Jacob Wakeling joined Posh from Swindon Town just ahead of the summer transfer deadline in 2024 following the expected departure of Jonson Clarke-Harris to Bristol Rovers. Unfortunately for Jacob, that transfer didn't materialise and a combination of injuries and being cup-tied for the Bristol Street Motors Trophy games meant first team exposure was limited during the 2023-2024 campaign.

He returned for pre-season in the summer of 2024 fit and raring to go and was the leading goal-scorer during pre-season before joining Sky Bet League Two side Gillingham on a season-long loan, scoring on his debut for the Gills in a 4-1 victory.