Middlesbrough will be forced to dip into the loan market after attempts to sign Muhamed Besic and Yannick Bolasie collapsed.
Boro appeared nailed on to re-sign Besic, 25, following the Bosnian midfielder’s impressive loan spell at the end of last season.
A fee of £6million had reportedly been agreed between the two clubs, as well as personal terms, only for the deal to stall due to a disagreement over agent fees.
Boro then launched a late bid for Millwall duo George Saville and Jed Wallace, which was rejected before the 5pm deadline.
They also missed out on Everton winger Yannick Bolasie, with the Toffees only willing to sell the winger on a permanent deal.
EFL clubs are still allowed to sign players on loan until August 31, meaning Besic could still sign for Boro before the end of the month.
The Bosnian international became a fans’ favourite at the Riverside, after helping Tony Pulis’ side secure a spot in the play-offs.
He made 17 appearances for Boro following his arrival in January.
His ability to break up play and run with the ball was key in the middle of the park.
Besic will also be keen to leave Everton, where he still appears to be surplus to requirements under new manager Marco Silva.
The midfielder signed for the Toffees in 2014 but has fallen out of favour after an injury-hit spell at Goodison Park.
Pulis will also be hoping to add more attacking options to his squad following the sales of Patrick Bamford and Adama Traore.
Jordan Hugill arrived on a season-long loan from West Ham on Tuesday and will provide competition to Britt Assombalonga and Martin Braithwaite up front.
Boro have also been linked with West Ham’s Sam Byram and Everton’s Cuco Martina, with both defenders potentially available on loan.
Both can operate as wing-backs in a 3-5-2 formation, which Pulis deployed in Boro’s 3-0 victory over Sheffield United on Tuesday night.
Boro’s only business on deadline day saw goalkeeper Connor Ripley, 25, sign for Accrington Stanley on a season-long loan.