Tottenham Hotspur's meek Champions League elimination not only ensured another trophyless season, but it also meant that when owners ENIC and chairman Daniel Levy celebrate their 20th anniversary at the helm, there will be just one piece of silverware to reflect on.
The 2008 League Cup remains the only trophy Spurs have lifted since Alan Sugar sold over half of his stake to the English National Investment Company, floated on the London Stock Exchange as ENIC plc in 1997, for £21.9m in December 2000, with Levy taking over the chairmanship two months later. An 80p-per-share price valued the club at £60m and anybody wanting to buy Tottenham now would have to bid in the region of $2bn. Their £1bn stadium, which is approaching its first "birthday", and state-of-the-art training ground are the envy of clubs across Europe, so Levy and ENIC can argue with plenty of justification that they have been doing something right.
However, qualification for next season's Champions League looks beyond Tottenham, Harry Kane's future is in real doubt for the first time and the club's transfer budget will once again be smaller than most of their rivals'. Head coach Jose Mourinho has warned he does not expect to undertake a summer overhaul of the squad and it is hard to find evidence to support the belief of the Portuguese that he will win a trophy during his Spurs tenure.
Since producing miracles at Porto, Mourinho has won with the best squads and biggest budgets in the leagues in which he has operated. Tottenham have neither, so the self-proclaimed "Special One" must find a different way if he is to deliver on his promise.
As Levy pointed out himself in a recent meeting with the Tottenham Supporters' Trust, the club have spent 13 out of the last 14 years in European competition. There have been Champions League and League Cup finals, as well as FA Cup semi-finals, and players such as Dimitar Berbatov, Luka Modric, Gareth Bale and Kane for fans to watch every week.
Levy also stressed that no club has a right to win trophies, but all of Spurs' main rivals have done so since the 2008 League Cup success, with Wigan Athletic, Birmingham City and Swansea City also winning silverware.
Opportunities have undoubtedly been missed. There was the summer of 2016, after Tottenham had involved themselves in an unexpected title challenge with shock champions Leicester City, when Mauricio Pochettino thought he could sign Sadio Mane from Southampton and Georginio Wijnaldum, then at Newcastle United. Both players moved to Liverpool instead and the rest, as they say, is history.
Pochettino wanted to overhaul his playing staff, but Levy eventually opted to put his faith in a decaying squad instead of his coach and took the cheaper option of replacing him with a man he hoped would guarantee trophies - if not always style.
That already looks questionable, even though it is too early to fairly judge Mourinho's work. His appointment has not yet produced the desired effect, but the continuing decline of players such as goalkeeper Hugo Lloris and Toby Alderweireld was once again in evidence in Germany. Mourinho claimed the entire Leipzig bench would currently play in his Spurs team, an incredible declaration, despite the sizeable injury list.
When presenting the new stadium, Levy said: "I'm always there to protect the club. I would say that the last 18 years, this club has definitely gone forward. You have your ups and downs but I think we've created the infrastructure here to become one of the biggest clubs in the world."
Levy is right, Tottenham have gone forward, but Mourinho perhaps put it best when he was this week asked whether, without Kane and Son Heung-min, overturning a first-leg deficit against Leipzig would have constituted one of his finest achievements.
"The achievements that stay forever are the victories," said Mourinho. "Less than winning is not a big achievement."
Tottenham fans who believe one trophy in 20 years will represent being short-changed on their sky-high season ticket prices will no doubt agree.
And it is hard to see how a squad so used to "less than winning" can reverse the trend for ENIC and Levy. (© Daily Telegraph, London)