In 2009, three of England's elite - Manchester United, Chelsea and Arsenal - progressed to the semi-final of the Champions League for the third successive season.
Despite three Premier League teams reaching the knockout stages this season, very few expect such a feat to be repeated.
With Manchester City the only side to win their group and United demoted to the Europa League, what has happened to English clubs in Europe?
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RISE OF EUROPEAN GIANTS
A few years ago, sides would only try to avoid the likes of Barcelona, Real Madrid and Bayern Munich.
Now, however, the improvement of teams like Atletico Madrid, Juventus and Paris Saint-Germain means that every group winner is a side England's representatives will struggle against.
Take a look at Arsenal. The Gunners have consistently progressed to the group stages for the last 16 seasons but, ironically, Arsene Wenger's side have failed to surpass the last 16 in each of the last five.
Wenger will be hoping for a kind draw on Monday, but after their inexcusable loss to Monaco last season, even that might not be enough.
LACK OF WORLD-CLASS PLAYERS
Back in 2009, United had arguably the world's greatest player, Cristiano Ronaldo, amongst their ranks. Now, they are reliant on an out-of-form Wayne Rooney and a 20-year-old striker in Anthony Martial for their goals.
Similarly, Chelsea's side included Didier Drogba in his prime. Diego Costa may have looked more like his old self recently, but there's no comparison between the Blues' current squad and the one they had six years ago.
Of the countries with teams in the Champions League, England are the only nation to not enforce a two-week break during the winter period.
The latter stages of the Europe's elite competition begin in February - by this time, English sides have played 26 games in the league alone, compared to La Liga sides, who will have played just 23.
The intensity of the Premier League, combined with no break, leads to fatigue by the time they get to playing the best European sides.
A Christmas break should be implemented not only for England's international side but for English clubs to get back to winning ways in the Champions League.