The Scottish full-back was tipped for a bright future at White Hart Lane when he was snapped up for around £9million from Rangers in January 2008.
Unfortunately, things did not go entirely to plan for him in North London and he soon tumbled down the pecking order.
"It was hard at times because the team were doing really well, they were winning a lot of games, so everyone was finding it tough," the 26-year-old told Sky Sports News.
"I knew there were top internationals playing at any one moment, but it was just a case of having a chat every now and again and knowing you were still needed and your time would come.
"It was tough though. I came down and maybe played six matches before I got injured and was out for the best part of a year. It was as if I had been put in the background a bit, so when I got another chance I was determined to take it."