Out on loan at QPR, the Republic of Ireland under-21 international lined up for Rangers at the Millennium Stadium against Cardiff in the Division Two final. Fortune appeared to be smiling on him as the Loftus Road side were undefeated in all the previous games he featured in.
A tight, tense affair in Cardiff looked like going the distance but, after 114 minutes, Andy Campbell pounced for the Bluebirds and QPR's dream of a Division One return was over for another year and Stephen admits he was left desolate.
"It was horrible," he recalled. "The worst feeling I have ever experienced in football, to be honest. It was a terrible feeling at the end - especially with the way it happened in the last few minutes of extra time.
"It was a killer, an absolute killer. The lads who have at the club since they were kids were devastated. It was the biggest game of their careers and I was so lucky to be involved in a game like that in my first time in league football."
Stephen added that even the fact that he knew he would be returning to Spurs in pre-season did little to lessen the pain of defeat that keeps Rangers in Division Two.
"At the time it still hurt just as much as anybody else, but they know that next season QPR will still be in the second division. You never know though, I could end up going back there again on loan.
"All the players were building up for such a big game and I think they might be a bit disheartened going into pre-season. Such a great season and still in the second division - it will be tough for them."
At the tender footballing age of just 19, defensive prospect Stephen Kelly has already sampled perhaps the most galling experience in the English game - defeat in a play-off final.