Calvin Ramsay was signed June 2022 as back-up for Trent Alexander-Arnold at right-back. Ramsay progressed through his home city club's youth ranks and became part of the first team set up in 2020/21, making four substitute appearances towards the end of the season. For 2021/22 he was the club's first choice right-back but missed two months before Christmas due to a hamstring injury. Ramsay was, however, named as the Scottish Football Writers Young player of the season and made his international under-21 debut.

Liverpool signed Ramsay in a deal worth an initial £4.2 million but with add-ons and a sell-on clause. His pre-season was disrupted by a back problem diagnosed during his medical. Outings were limited to a brief substitute appearance against Napoli in the Champions League and playing all ninety minutes of a Carabao Cup tie with Derby County. Both these games were in November, a month in which he also made his full Scotland debut. In February 2023 Ramsay had knee surgery which ruled him out for the rest of the campaign but he vowed to rest, recover and come back stronger. A loan deal was then agreed for Ramsay to spend 2023/24 with Championship side Preston, but he hardly featured due to knee injury and was recalled in January. Ramsay joined Bolton Wanderers on loan for the remainder of the 2023/24 season but only played in four matches. 

In the summer of 2024, shortly after the arrival of Arne Slot as head coach, Ramsay joined League One club Wigan Athletic on loan for the whole of the 2024/25 season, but returned in January after just three league starts. On 13 January it was announced that Ramsay would spend the rest of the season on loan at Kilmarnock in his native Scotland. He again struggled for game time, being taken off at half time of his first start at Hearts and after that being limited to just eight substitute appearances.