Juventus 2-2 Chelsea, Champions League round of 16, February 2009
One of Hiddink’s first matches in charge was a second leg Champions League clash against Italian giants Juventus.
After scraping a 1-0 win at Stamford Bridge, the tie was far from over and would be decided in Turin. Chelsea rallied that night, coming from behind twice to draw 2-2, and advance to the quarter-finals 3-2 on aggregate.
Hiddink’s opposite number that night was Claudio Ranieri, who is currently hoping to lead his Leicester side to Premier League glory against all odds this season.
Chelsea 4-4 Liverpool, Champions League quarter-finals, April 2009
Another Champions League clash, as Chelsea faced more familiar opponents, Liverpool.
Things were looking good for the Blues, who took a 3-1 lead to Stamford Bridge.
Chelsea found themselves 2-0 down at the break and another Liverpool goal would have meant Hiddink’s side heading out of the competition in what looked like a sensational turnaround. But the home side clawed it back to 2-2, thanks to goals from Drogba and an Alex free-kick.
Frank Lampard then put Chelsea ahead, before Liverpool turned the tie on its head again, making it 4-3 on the night with less than 10 minutes to go. Lampard then struck again to level the game, and Chelsea advanced 7-5 on aggregate.
Renowned as one of the most memorable Champions League games in recent years, the result saw Chelsea through to the semi-finals for the second year running.
Arsenal 1-4 Chelsea, Premier League, May 2009
Following Champions League elimination at the hands of Barcelona a few days before travelling to Arsenal, Chelsea were hoping for a win that would secure automatic qualification for next season’s tournament.
Arsenal themselves had been knocked out at the same stage, so it was all to play for at the Emirates.
Hiddink showed a tactical masterclass as Chelsea romped to a 4-1 win, handing Arsenal their heaviest ever home defeat at the Emirates.
Goals from Alex, Nicolas Anelka and a misfortunate Kolo Toure own goal saw Chelsea take a 3-0 lead before Arsenal pulled one back. Florent Malouda secured the points with five minutes to go.
With the win, Chelsea were guaranteed a top three finish and automatic qualification to the Champions League.
Chelsea 2-0 Blackburn Rovers, Premier League, May 2009
Hiddink’s final home game in charge of the Blues was a comfortable 2-0 win against Blackburn Rovers.
The crowd were chanting the Dutchman’s name all afternoon, and cards and banners begging him to stay were visible throughout.
Hiddink later suggested he had second thoughts about leaving, and admitted that the warm reaction from Chelsea fans was surprising.
Everton 1-2 Chelsea, FA Cup final, May 2009
Hiddink’s first spell as Chelsea boss ended in the perfect way, as he led his team to FA Cup glory in the scorching summer heat at Wembley.
Louis Saha stunned the Blues, scoring after just 25 seconds, but goals from Didier Drogba and Frank Lampard turned the game around, as Chelsea won their fifth FA Cup.
After lifting the trophy with his team on the pitch, before smoking a cigar in the dressing room, Hiddink bowed out as Chelsea boss.
Fans will be hoping he will end this tenure in a similar fashion as the Blues chase FA Cup and Champions League glory once again under the Dutchman.
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