Less than 20 weeks separated that night in Amsterdam when Mauricio Pochettino left the field with his tie askew, tears in his eyes and a team in the Champions League final, and then Tuesday when he was obliged to get off quick or get caught up in a Colchester pitch invasion.
Not every cup tie can be like the great comeback against Ajax that propelled Tottenham into their first Champions League final, and not many managers over the years avoid the ignominy of a cup shock, like Spurs' midweek misadventure.
It was only the Carabao Cup but the losing boss' press conference utterances still linger.
Yet another night of Pochettisms, those remarks in good times and bad that set alarm bells ringing all over Spurs, from his chairman Daniel Levy, to the players who've committed their futures and, one might assume, those who have not.
What does the manager mean when he says that there are "different agendas" among his squad? And what exactly is his own, other than to intermittently stoke the debate about how long he will be there, who among the players will stay and what the future might hold?
Over it all hangs the spectre of What Might Harry Do, if Kane decides that there is no prospect of winning the trophies that are absent so far from his CV. It is a difficult situation, but not impossible, and a consequence of the considerable progress that Spurs have made with Pochettino.
Increasingly, however, the greatest source of instability seems to be the manager himself, or rather his habit of alluding to problems behind the scenes that he perceives to affect his own future and, as a result, that of his players.
On Tuesday it appeared to be a direct attack on those players expected to leave in the summer, among them Christian Eriksen, a second-half substitute whose shoot-out penalty was saved.
"Maybe our performances are good," Pochettino said, "but you need this extra, which is mental, connection. It's energy to be all together, not to have different agendas in the squad."
He has been at it for more than a year now, a kind of internal monologue that the affable Argentina native seems unable to stop flowing over into his public statements for reasons that are not clear.
Almost as soon as Spurs had won that Champions League semi-final second leg against Ajax in May, Pochettino returned to the pre-match ambiguity about his future. As to whether Spurs could expect to compete without a new five-year plan, he reflected: "I think we would be very naive."
The build-up had been dominated by his future, after he suggested that should his team reach the final it would be a grand idea to close the chapter and leave on a high.
There were chances after that to clarify, but Pochettino prefers to leave it open to interpretation.
In late July, after a friendly win over Real Madrid, Pochettino wondered aloud whether his title should be changed back to head coach from manager, such was his professed ignorance of the club's transfer dealings.
Before that, in China, he had ruminated on leaving Spurs had the Champions League final been won. "If the result had been different," he said then, "maybe you can think it is a moment to step out of the club".
You might say that it began in May 2018 when, after a daft last-day-of-the-season 5-4 win over Leicester City, he launched into his first major public inquest. Then he urged the club to "tell the truth" about the financial situation, and also to be "brave and take risks".
The delivery was surprising, but not perhaps, as surprising as the consequences. If this was a demand for Levy to invest in the team then the effect was very different. It was another three windows before Spurs signed a new player, but it was only 11 days before Pochettino signed a new contract.
There is still the best part of four seasons left to run on that deal and in the interim the jobs at Real Madrid and Manchester United have become available and others appointed. A dinner with Levy in late August has been cited as a peace summit, but one still asks where it is that Pochettino sees himself in a year's time. A hard question to answer these days because his list of grievances seems so broad.
Tuesday was one of those bad nights that all managers have, although ultimately the season will not be judged on the Carabao Cup.
What Pochettino has to say in those situations is a different matter: that carries with it a significant effect, for his players and his club alike.