Jake joined the Mariners on a two-year deal in the summer of 2023, returning to Blundell Park after a previous loan spell with Town in 2021.

A Sheffield Wednesday fan, Eastwood came through the youth system at their cross-city rivals in Sheffield United and made his senior first-team debut for the Blades in August 2017. Despite being contracted to the Brammall Lane club from 2016 to this summer, he made just the one league appearance for the club and, instead, took in several loan spells.

Eleven temporary switches preceded his permanent move to Blundell Park this summer, reuniting him with Paul Hurst after being managed by him in his spell with Town during lockdown.