Newcastle Midfielder Hatem Ben Arfa signed a last-minute loan deal to go to Hull, and defender Mapou Yanga-Mbiwa went to Roma on a season-long loan.
Sunderland Defender Sebastien Coates joined on loan from Liverpool, as did Ricardo Alvarez from Inter Milan.
Valentin Roberge joined Reims on a season-long loan and Modibo Diakite left by mutual consent.
Middlesbrough Jelle Vossen signed on a season-long loan from Genk. Yanic Wildschut signed a two-year deal from Heerenveen, and Jamal Blackman arrived on loan from Chelsea.
Seb Hines joined Coventry on loan.
Hartlepool Luke James has signed for Peterborough for an undisclosed fee.
Middlesbrough 2-3 Sheffield Wednesday
Southend United 1-2 Hartlepool United
Exeter City 1-1 York City
Middlesbrough boss Aitor Karanka remains hopeful of adding to his squad before the transfer window closes.
The club are trying to secure a loan deal for Chelsea striker Patrick Bamford and Karanka revealed he's also chasing another new signing.
Middlesbrough midfielder Richard Smallwood as joined Rotherham United on an emergency loan deal.
If the move is ratified by the Football League, the 23-year-old will go straight into Rotherham's squad for tonight's game against Watford.
Smallwood spent the second-half of last season on loan at Rotherham, helping the club achieve promotion to the Championship via the playoffs.
Middlesbrough FC are about to complete the transfer of 25-year-old midfielder Adam Clayton, from Huddersfield. Jacob Butterfield is expected to move in the opposite direction.
Middlesbrough got off to a winning start in the new Championship season with a 2-0 win over Birmingham at the Riverside.
Spanish defender Daniel Ayala headed in Grant Leadbitter's corner to put Boro in front after 33 mins. Enquire 'Kike' Garcia then doubled the advantage with a debut goal after Lee Tomlin's deflected shot fell kindly for the Spaniard.
In League Two, Hartlepool United were beaten 1-0 by Stevenage. While York City were held to a 1-1 draw at Tranmere. Keith Lowe had put the Minstermen in front via a first-half corner but James Rowe grabbed a late equaliser for the hosts.
Middlesbrough boss Aitor Karanka is eager for the club to make a good start to the new campaign.
Boro finished 12th in the Championship last season but won six of their last eight games.
Karanka is keen for his side continue that form into the new season. Middlesbrough host Birmingham at the Riverside today.
Middlesbrough defender Kenneth Omeruo has expressed his delight over his return to the club.
The 20-year-old, who spent the second-half of last season at the Riverside, has re-joined Middlesbrough on a season-long loan from Chelsea.
Omeruo played in all four of Nigeria's games at the World Cup in Brazil.