Still only 24, Ryan was just 17 when he stepped out at NEC Nijmegen in the UEFA Cup on November 27, 2008.
It was only a fleeting glance of what was finally to come for Enfield-born Ryan as Jamie O’Hara headed home the winner in Holland.
We went on to reach the last 32, where we were beaten by Shakhtar Donetsk. Meanwhile, Ryan was an ever-present with 28 games, scoring 28 goals as our Under-18s won their division of the Premier Academy League in 2008-09.
Fast-forward seven years and Ryan is a key member of Mauricio Pochettino's squad having made his first team breakthrough and eventually playing 37 matches in all competitions.
As we prepare to step back into Europa League action against Anderlecht this evening, Ryan recalled that night in Holland.
“It seems remarkable,” he said. “It feels like I was a little boy back then!
“A lot of time has passed since then. I remember I just wanted to get on. I was banging in goals for the youth team at the time and felt like I deserved a chance.
“I got on for a few minutes on the end. It meant a lot. I remember running out and the fans were singing my name. It was a special moment and one I’ll never forget.”
Below: Ryan speaks to Spurs TV
Moving back to the present, Ryan echoed the thoughts of a squad determined to put right our loss against Anderlecht in Brussels a fortnight ago.
“We were disappointed with what happened at Anderlecht,” he said. “We want to do well in this competition so to blow a lead like that (we led 1-0, lost 2-1) and the way the game went was a bit of a kick in the teeth.
“We’re eager to do well in this competition. In the last few years we’ve gone out earlier than we wanted. We want to go far and gain that experience so this is a big game for us.”