It is only right to reserve judgement on Tottenham's transfer window until after 11pm on Monday night but clearly it has been a difficult 24 hours for the club.
Adama Traore, a Spurs target for the entire month, has chosen Barcelona, while Liverpool look set to beat their Premier League rivals to the signing of Porto winger Luis Diaz.
There is no great shame in being gazumped by two of the biggest clubs in the world but the situations raise further questions about Spurs' recruitment strategy, and leave embattled chairman Daniel Levy and managing director Fabio Paratici under even more pressure going into the final days of the window.
Adama opted to return to Barca on loan from Wolves amid reported concerns over playing right wing-back for Spurs, although economics also appear to be a factor in the move.
The Catalan club are willing to pay nearly £30million for the Spain international in the summer, a significant fee for a player with 18 months on his contract – and one likely considered extravagant by Spurs, particularly given concerns over Adama's end product.
As for Diaz, Spurs were prepared to meet Porto's £50m asking price but the Colombian winger and his representatives preferred a move to Champions League Liverpool.
The Reds had made Diaz their top target for the summer but brought forward their interest after Spurs' approach.
Spurs, of course, faced Liverpool in the 2019 Champions League final but the trajectories of the clubs before and since have been starkly contrasting.
This week's disappointments in the market reflect Spurs' current position – Europa Conference League drop-outs – and are another consequence of the club's failure to really seize the initiative when Mauricio Pochettino was in charge.
In isolation, missing out on Adama and Diaz is no disaster – there were legitimate questions about where both would have fit into Antonio Conte's squad – but they join a lengthy list of missed targets, reflecting a concerning pattern in the transfer market.
Under Levy, Spurs have always preferred to move late in the window, but the strategy has seemed to decrease in effectiveness over time and leaves them vulnerable if deals break down, as the last 24 hours has illustrated.
Paratici, as an experienced sporting director, has had seven months to put a more coherent and proactive transfer strategy in place to address the glaring issues in the first-team squad, but Spurs' approach in the market still appears hopeful and scattergun.
Granted, January is never an easy time to buy players and few Premier League clubs have done significant business. But equally, few are under as much pressure to sign players as Spurs, and Aston Villa's quietly effective business this month offers an example of an alternative. It doesn't always have to be this way.
There is a danger that Spurs' January could come to resemble their chaotic search for a permanent successor to Jose Mourinho in the summer, when Levy and Paratici veered between targets without success, eventually settling for Nuno Espirito Santo – with disastrous consequences.
The capture of Conte as Nuno's successor was a smooth operation, albeit after a failed attempt to appoint the Italian in the summer, but there has been little else since Paratici's appointment to suggest there is joined-up thinking at the top of the club.
In fairness, Paratici is also tasked with clearing up a mess he inherited, namely moving on Tanguy Ndombele, Giovani Lo Celso and Dele Alli, none of whom are wanted by Conte, and Levy has pulled off transfer coups in recent years, including for Ndombele and Cristian Romero in the summer.
There is still time for Spurs to pull a rabbit out of the hat and finish the month with a stronger squad, boosting their chances of a top-four finish under Conte.
But after their double blow, time is fast running out to ensure this window does not end in disappointment.
