The 27-year-old has been to two finals, one of which ended in defeat and the other a victory in which he did not get on the pitch.
Liverpool's first final for five years, and their first trip to Wembley since 1995, probably represents Downing's best chance of the three to finally experience victory.
Npower championship high-fliers Cardiff, no strangers to Wembley themselves as this will be their third appearance in five years having lost the 2008 FA Cup final and 2010 Championship play-off, will obviously have other ideas.
But having watched from the bench in 2004 as Middlesbrough beat Bolton and then played in Aston Villa's defeat to Manchester United two years ago the England international is keen to make amends.
"The first one I was an unused sub for Middlesbrough. I would have liked to have played but I was still involved," he said.
"The second one for Villa against United - a few things didn't go our way.
"Nemanja Vidic could have been sent off early on and we were a little bit unlucky on the day.
"It would have been nice to finish with a medal but it wasn't to be.
"Hopefully this time around I'll get one."
Downing played in Liverpool's first Carling Cup tie this season, at Exeter, but was an unused substitute for the next round at Brighton and did not feature again until the two-legged semi-final against Manchester City.
After a bright start to his career at Anfield following his £20million summer move from Villa Downing's level of performance dropped and he has discovered a regular place is not something to be taken for granted.
But the winger is spurred on by the reminder of how tough it has been for the club - who did not have a home match until the second leg of the semi-final - to get to the verge of winning their first silverware since the 2006 FA Cup.
"You work hard to get there with the trips away to Exeter and Brighton - they stick in your mind," he told liverpoolfc.tv.
"They were hard games so it'd be nice to finish the job off at Wembley."
Defender Martin Skrtel is keen to end his - and the club's trophy drought - with a Carling Cup victory.
The Slovakian arrived at Anfield in January 2008 so this will be his first final in a red shirt.
"Everybody plays football to win medals and trophies. Now we have a big final coming up and I have a chance to win my first trophy with Liverpool," he told LFC Magazine.
"I believe we will win, but I know it won't be easy. I think it will be a very difficult game but I think we can get the cup.
"At the start of the season our targets were to qualify for the Champions League and to win some trophies.
"Our targets are still reachable."