To end the transfer window having bought only Marouane Fellaini for £27.5m, an embarrassing £4m more than the Everton midfielder's buyout clause, heaps unwanted ignominy on Manchester United and Ed Woodward, the new executive vice-chairman.

This was the summer that began with David Moyes being billed as the Chosen One as Sir Alex Ferguson's successor and Woodward proclaiming there were sizeable funds at the manager's disposal. Yet three months later Monday's 11pm deadline was only minutes away and Moyes and Woodward faced having no major signing to parade in a doomsday scenario that was averted by Fellaini's arrival, but with the deal to buy Athletic Bilbao's Ander Herrera having collapsed.

Against a bizarre backdrop of imposters supposedly posing as United representatives, Woodward had decided Herrera's €36m (£30.5m) buyout clause was too much and continued to haggle even when it was made clear the Basque club would not budge.

This all followed the earlier failures of United's transfer policy. At the start of the window Moyes told Woodward to target Barcelona's Cesc Fábregas and Thiago Alcantara, while some sections of the executive wondered how sorely the experience of David Gill, the vice-chairman's predecessor, would be missed.

When Alcantara chose Bayern Munich and Fábregas decided to stay at Barca, an answer began to emerge. To his credit Moyes was always conscious this would be the trickiest window of his tenure due to the surgery needed on the squad – two central midfielders, at least, were needed – and the challenge presented in attracting players now the Ferguson factor was gone. Yet the strategy adopted by Woodward appeared scattergun and formed on the hoof, at best, with furious United fans characterising it far more scathingly.

The move for Herrera occurred only late last week when Athletic's president, Josu Urrutia, revealed a €30m (£25.6m) bid had been rejected. Given what Woodward's research into the 23-year-old and Athletic would have shown, he should have known the offer would be knocked back. As the club use solely Basque players the logical conclusion was it would only sell if forced to by a bid for the full €36m amount of the clause.

Yet though Woodward continued to believe the player was over-priced, given the earlier failures over Thiago and Fabregas, a strong argument runs he might have decided that Herrera was, indeed, worth paying €6m more than United's first bid to ensure Moyes's midfield was strengthened.

Here, he might have learned a lesson from the earlier dallying over Fellaini. When Moyes finally decided he wanted the Belgian, the ploy the manager and Woodward came up with was to wait until his £23.5m buyout clause expired on 31 July and then try and buy him on the cheap. This was further confused by marrying the offer with a move for Fellaini's club colleague Leighton Baines in a barely credible £28m joint valuation that Everton described as "derisory" and "insulting", a description aimed squarely at Moyes as their former manager of 11 years.

That was in mid-August. Fast forward to this weekend and United were still pursuing the twin-offer approach despite all the noises from Goodison Park being that Everton's chairman, Bill Kenwright, was intent on keeping Baines but less resolute regarding Fellaini.

Only on Monday did Woodward finally decide to split the bids. Yet the £15m he proposed for Baines was rejected – probably because it was exactly, and bafflingly, the same valuation of the left-back turned down in the weekend's joint £40m offer – to leave United pursuing Fellaini, who finally arrived for £4m more than his release clause. Given Moyes, as the former Everton manager who signed Fellaini, had inserted the clause and knew the Belgian's contract intimately this does not seem great business.

Woodward, in particular, comes out of United's experience in the summer market bruised, having endured a tough baptism as the lead mover and shaker in the cut-throat arena of global transfer dealing.

As Arsenal's Arsène Wenger landed Real Madrid's Mesut Ozil for a cool £42.5m to throw off his mantle as ditherer-in-chief of the Premier League, Woodward – and Moyes – have been left with their hopes of making a marquee signing to begin his tenure as manager in tatters.

After Sunday's 1-0 defeat at Liverpool, Moyes claimed no concern if no-one was bought. This was avoided in Fellaini's acquisition, but he and Woodward will have to think seriously about January's winter window and beyond. A sizeable section of the United support took to Twitter late on Monday evening to describe their club as a laughing stock. Woodward and Moyes will be determined there can be no repeats in future.