Sunday's Community Shield clash represents Liverpool's return to the competition for the first time in 13 years.
It is the traditional curtain-raiser of the English football calendar, pitting the league champions against the FA Cup holders.
This year, with Pep Guardiola's Manchester City sweeping all before them on the domestic front, the league runners-up (and European champions) will provide the opposition.
Having been edged out by a single point to the title, it is scant consolation to Jurgen Klopp and Liverpool.
On that August afternoon in 2006, goals from John-Arne Riise and Peter Crouch were enough for Rafa Benitez's FA Cup winners against Jose Mourinho's dominant Chelsea side.
That day in Cardiff saw a rather surprising line-up, and four new signings... and the team looks very different to today's.
Pepe Reina (Goalkeeper)
Fresh from his FA Cup final heroics where he saved three of West Ham's four penalties, Reina was Liverpool's undisputed No 1. It was another impressive season for the Spanish shot-stopper who reclaimed the Premier League's Golden Glove Award with 19 clean sheets.
Steve Finnan (Right back)
The Irishman developed into Mr Dependable under Benitez and had been a mainstay of the side in the three years since his arrival from Fulham. The arrival of Alvaro Arbeloa in January 2007 limited his game-time and ultimately led to his departure two years later.
Jamie Carragher (Centre back)
Captain for the day with Steven Gerrard left on the bench. Carragher was 28 and at the peak of his powers in 2006. Fresh from the disappointment of missing a penalty in England's World Cup shootout defeat by Portugal, Carragher put it behind him with another sterling season in red.
Daniel Agger (Centre back)
A £6m signing from Brondby in January 2006, the 2006-07 season was a coming of age for the great Dane. He dislodged Sami Hyypia as first-choice centre-back alongside Carragher, but persistent injury problems limited him to just 232 appearances in nine seasons.
John-Arne Riise (Left back)
In the ninth minute Riise raced from just outside his own area to belt a trademark left-footed piledriver past Carlo Cudicini to give Liverpool the lead. Competition for the left back slot had arrived that summer in the shape of Fabio Aurelio, but this was a promising start.
Jermaine Pennant (Right midfield)
The most left-field of Benitez's summer signings ended up at right wing. Pennant arrived for another shot at a big club after a £6m move from Birmingham. A promising debut campaign brought 52 appearances and a leading role in the Champions League final defeat by AC Milan. Made only a further 29 appearances in the next 18 months as the move turned sour.
Momo Sissoko (Central midfield)
A fan favourite due to his all-action, fully-committed displays. Sissoko looked set to be the bedrock of Liverpool's midfield after an impressive debut campaign. But by this point his performances had begun to tail off after a horrific eye injury and the arrival of Javier Mascherano midway through the season saw him fall down the pecking order.
Bolo Zenden (Central midfield)
Dutch international turned 30 just two days after this game and his career was well and truly slowing down by this point. A utility player, he had lost the pace that made him a flying winger in his early days at PSV Eindhoven and Barcelona. Started both semi-finals against Chelsea and then the final before he was released at the end of his contract.
Mark Gonzalez (Left midfield)
Much was expected of electric Chilean winger Mark Gonzalez, whose Anfield move had been delayed by 12 months due to work permit issues. Scored a vital late winner in a Champions League qualifier against Maccabi Haifa in midweek but his career on Merseyside never took off and he was sold to Real Betis after just one season.
Luis Garcia (Second striker)
A hero of Liverpool's Champions League success and one of few genuine creative sparks in Benitez's squad. It proved to be his final season on Merseyside - 12 months later he was used as a makeweight in the deal to bring Fernando Torres to Anfield.
Peter Crouch (Centre forward)
Crouch was a popular figure up and down the country after his Robot celebration proved immeasurably more memorable than England's shambolic World Cup campaign. Won the game with a back-post header from a Craig Bellamy cross deep into the second-half after losing his marker, John Terry. The arrival of Dirk Kuyt later in the month limited his game time but he still went on to be the club's leading scorer that season with 18 goals in all competitions.
Substitutes
Fabio Aurelio, Steven Gerrard, Xabi Alonso, Craig Bellamy, Florent Sinama-Pongolle
Aurelio proved a shrewd acquisition on a free transfer from Valencia, with only injuries denying him more than the 87 league appearances he made in six years.
Gerrard and Alonso had been left on the bench after their World Cup exploits but returned to form the crux of Liverpool's midfield.
Bellamy had scored on his debut against Maccabi Haifa and provided the assist for Crouch but he was unable to convince Benitez of his long-term worth and left after just one season. Returned to the club in August 2011 for another season, this time under Kenny Dalglish.
This proved to be Florent Sinama-Pongolle's final Liverpool appearance having failed to deliver on the promise Gerard Houllier had spotted in an Under 17 World Championship.
What happened next?
Victory in the Community Shield isn't always an indicator of good times to come. Liverpool's Premier League performances deteriorated in 2006-07.
A third-place finish secured another season of Champions League football, but a return of 68 points and 10 defeats was a disappointment after the success of the previous season.
Benitez struggled to find his best XI within a bloated squad, and how to get the best out of Gerrard, who had reverted back to central midfield after starring on the right in 2005-06.
The mid-season arrivals of Javier Mascherano and Alvaro Arbeloa proved key in shaping the peak Benitez side of 2008-09.
It was a different story on the continent as Liverpool overturned European champions Barcelona to make a second Champions League final in three years.
This time Milan had their revenge, with Filippo Inzaghi's brace securing a seventh title for the Italian giants.