Grindlay began his career as a youth player for Celtic before being picked up by Newcastle United. He was primarily in the youth system, however he did make one appearance in a friendly match with the first team against Berwick Rangers when he was 19. He left and had a spell with Grimsby Town. This was brief and soon returned home, with his family at Dumbarton.
Dumbarton
Grindlay was shipped off on loan to Dumbarton Academy FPs during his first season to give him some regular football. He helped guide them to a domestic cup final at Hampden Park in Glasgow, losing 2–1. He returned and found himself immediately in the 1st team. He became one of Dumbarton's most experienced and highest paid players at such a young age, making nearly 200 appearances and setting records along the way. In 2004, he won the Dick Jackson Memorial Shield, an award given to players by supporters for being the best young player at the club.[2] On 7 April 2007 he kept his 15th clean sheet of the season, breaking a record set back during the 1991–92 season.
Queen of the South
After leaving Dumbarton, Grindlay signed for First Division side Queen of the South on 9 July 2007. He made four appearances for the club.
Ayr United
Grindlay was snapped up by Ayr United boss Brian Reid after his release from Queen of the South. Grindlay played in every game in the 2008–09 Season as Ayr went up via the Play-Offs. On 10 January 2009 he saved an Allan Russell penalty in a 2-2 Scottish Cup draw with Kilmarnock.[3]
Dumbarton
Grindlay opted to take up a second spell with the Sons for the 2010–11 season, he has signed for another season at 'The Rock' in May 2011. During the 2011–12 season he was in fine form as he helped the Sons win promotion through the play-offs to make the First Division for the first time in 16 years. After re-signing with the club for the 2014–15 season, his 10th season with Dumbarton and was entitled to a Testimonial match. He had the following to say about his testimonial:[4]
"We will need to look to get a testimonial committee together and fingers crossed we can get a game and a few events arranged... It will be a good chance to get the players and the fans together for a day that everyone can enjoy."[4]
He left the club on the week of the testimonial at the end of his contract.[5]
