Ryan Donaldson first played for Pools as a teenager when Mick Wadsworth brought him to the Vic on a two month loan spell from Newcastle United. He left St James Park a year later and enjoyed spells at Gateshead and Plymouth on either side of a three year stay at Cambridge United, for whom he made goalscoring contributions to Wembley wins in the FA Trophy and National League playoff final. Donaldson signed for Pools in 2017 with the club reeling from its first ever relegation from the Football League. He was made club captain by Craig Hignett, a position he held for the remainder of his time at the Vic. With strong competition on the right hand side of the team, Donaldson struggled to hold down a first team spot in his last season with the club as Dave Challinor's side mounted a promotion push, but he remained a valued squad member on and off the pitch. His final contribution as a Pools player was a sudden death penalty in the nerve-shredding Playoff Final shootout against Torquay United at Ashton Gate. His seemingly nerveless spot kick proved decisive as Brad James saved Torquay's next effort to send Pools back to the Football League after a four year absence. Dave Challinor was keen to keep hold of Donaldson in the summer, but the player decided that this would be a fitting time to part company, and he turned down the offer of a new contract and left the club.