Eastwood joined the academy as an U14 back in the 2015-2016 season, and progressed through the ranks to become an U18 player for the 2018-2019 season as well as making one appearance for the U19s during the season.
Eastwood also got his first taste of men’s football during the 2018-2019 season, as he signed for Portishead Town’s B team and competed in the Weston & District Division Two side, finishing as top scorer for the side and recieving Portishead Town’s Young Player of the Season.
Eastwood’s form for the B team earned him a spot with the first team in March 2019, where he made seven appearances, scored one goal and was an unused substitute once during the final couple of months at the club.
In August 2019, Eastwood signed for Western League Premier Division side Clevedon Town and made one appearance, being an unused substitute once.
On 28th September 2019, Eastwood rejoined Portishead Town’s first team before dual registering with Weston on 21st October 2019. For Portishead this season, Eastwood featured in two games for the Western League Division One side.