However, despite Simao's agent, Jorge Baidek, claiming that the "operation is very advanced", Benfica's attempts to thwart the deal by driving a hard bargain succeeded. Simao flew back to Portugal as expected but the two clubs were in disagreement about the payment schedule for the 25-year-old, with Liverpool also resisting Benfica's attempts to take striker Djibril Cissé in return.
The failure to clinch the deal is a severe blow to the Liverpool manager, Rafael Benitez, who has been working hard on securing a right-sided midfield player. The fact that he was prepared to spend so much money on Simao showed how desperate he had become.
The attempt to sign the player was the biggest surprise of the final day of the transfer window. Everton appeared last night to have been thwarted in their attempts to top that by taking Robbie Keane from Tottenham Hotspur.
They did, however, sign the Netherlands winger Andy van der Meyde on a four-year contract from Internazionale for an undisclosed fee, thought to be £2.1m, after the 25-year-old finally passed a medical. Van der Meyde has been suffering from a groin strain.
Moyes had hoped to land Keane as well but the Irishman's move was always dependent on Spurs' success in bringing in a replacement striker. The Tottenham chairman, Daniel Levy, was in Italy trying to secure Cristiano Lucarelli from Livorno. The 29-year-old is eager to move to Spurs and had reacted angrily after the Serie A club rejected a £3.6m bid. He may move in January - unless an 11th hour deal was brokered last night.
Spurs were, as expected, the busiest club in the Premiership yesterday and were able to announce the signing of Jermaine Jenas from Newcastle United for £7m on a five-year deal.
Goalkeeper Paul Robinson - who is on England duty with Jenas - said: "I've seen Jermaine, he got back from his medical about 1.30am but he's looking forward to it. I don't think I needed to sell Spurs to Jermaine the way we are moving forward at the moment. The chairman and board are doing that nicely."
Jenas is set to partner Michael Carrick in the centre of midfield with Edgar Davids pushed to the left - which will put Andy Reid's place under threat. The width for Spurs will come from another new signing - the attacking left-back Lee Young-Pyo who has moved in a four-year deal worth up to £2m from PSV Eindhoven.
The 28-year-old South Korean international replaces Erik Edman who last night completed a move to Rennes, while Spurs have allowed another left-sided player, Reto Ziegler, to move on a season-long loan to Hamburg.
Another surprise move was the £2m Wigan Athletic paid for the Leicester City striker David Connolly. The price for the 28-year-old Republic of Ireland international could rise to £3m. "The move has come about very quickly but I'm delighted to be in the Premiership at last," Connolly said.
Middlesbrough were another club who were active yesterday with the Brazilian defensive midfielder Fabio Rochemback flying in to secure a five-year, £2.5m transfer from Barcelona. Middlesbrough have already applied for a work permit for the player, who is currently on loan at Sporting Lisbon, but Rochemback was still discussing terms.
"The offer from Middlesbrough is very good," Rochemback said before leaving Portugal. "A player has to play, that is it. If Sporting, Barça and Middlesbrough have accepted a deal then this is what is happening."
The Middlesbrough manager, Steve McClaren, was also hoping to rectify a move for Rangers' Peter Lovenkrands while defender Abel Xavier, who was a free agent, has also moved to the Riverside. At the same time, McClaren has allowed Dutch right-back Michael Reiziger to leave. He has agreed a two-year deal with PSV Eindhoven after being granted a free transfer.
Arsenal, meanwhile, have signed the Sunderland goalkeeper Mart Poom on loan as cover for Jens Lehmann - with the promising defender Justin Hoyte going in the opposite direction, also on loan, until the end of the season. "I'm absolutely thrilled to have him on board," said the Sunderland manager Mick McCarthy.
Also leaving Arsenal, again on loan, is David Bentley, who will move to Blackburn Rovers for the season after failing to find a permanent deal with a Premiership club. The Charlton Athletic striker Francis Jeffers was in talks with Rangers last night about a loan move as well.
A long-standing deal which was being resurrected was Bolton Wanderers' attempt to sign Southampton's Fabrice Fernandes after the Frenchman negotiated a deal allowing him to move on a free transfer.
Deals which have been blocked include two to Newcastle United - with Aston Villa rebuffing attempts to re-sign Nolberto Solano by demanding James Milner on loan in return, and Southampton setting too high a price, thought to be £1.5m, on 32-year-old defender Claus Lundekvam.
Leading Premiership transfers on deadline day
MICHAEL OWEN Striker: Newcastle United from Real Madrid £17m
JERMAINE JENAS Midfielder: Tottenham from Newcastle £7m
DAVID CONNOLLY Striker: Wigan Athletic from Leicester City £3m
LEE YOUNG-PYO Left-back: Tottenham from PSV Eindhoven £1.37m
ELVIS HAMMOND Striker: Leicester City from Fulham £350,000
ANDY VAN DER MEYDE Winger: Everton from Internazionale undisc.
ERIK EDMAN Left-back: Rennes from Tottenham undisc.
RURIK GISLASON Striker: Charlton Athletic from HK Kopavogur nominal
FRANK SONGO'O Striker: Portsmouth from Barcelona nominal
JOSEPH-DESIRE JOB Striker: Al Ittihad from Middlesbrough loan
MICHAEL REIZIGER Defender: PSV Eindhoven from Middlesbrough free
ZURAB KHIZANISHVILI Defender: Blackburn from Rangers loan
DAVID BENTLEY Forward: Blackburn Rovers from Arsenal loan
RETO ZIEGLER Winger: Hamburg SV from Tottenham loan
MART POOM Goalkeeper: Arsenal from Sunderland loan
JUSTIN HOYTE Right-back: Sunderland from Arsenal loan
EIRIK BAKKE Midfielder: Aston Villa from Leeds United loan
LIAM FONTAINE Defender: Yeovil Town from Fulham loanReuse content