The first transfer for the season was thought to have been announced back in May, with Maidstone United's England youth international defender Chris Smalling signing a two-year contract.

[15] Boro's midfield options were further reduced when Hérold Goulon, signed two years earlier, left without playing a senior game for the club.

Fans were disappointed with the sale but, coupled with Young's wish to make the move, the club felt the offer was too good to turn down, having only paid £2.5 million for him a year earlier.

[19][20] A replacement was brought in when Middlesbrough completed the £3 million signing of Arsenal's Justin Hoyte before the first game of the season, but not in time for him to be eligible to play.

[21] In mid-November, before the window opened, former youth goalkeeper David Knight returned to the club on a month-to-month contract as cover following an injury to third-choice keeper Jason Steele.

[26] With the transfer window open, Spurs put in a bid for the player, reported to be around £6 million, which was described as "derisory" by Middlesbrough chief executive Keith Lamb.

[28] Downing's father, Stewart Senior, revealed his son's reasons for submitting his transfer request, stating that "when he signed his new contract [in February 2008] he was assured that there would be significant investment in the squad", arguing this had not happened.

[34] Ross Turnbull left the club at the end of the season on a free transfer, to join Chelsea, after rejecting several contract offers, citing that he wanted to play regular first team football.

Boro looked set to record their first win at Anfield for thirty-two years until Jamie Carragher's shot deflected off Emanuel Pogatetz for an own goal with five minutes to go.

The visitors frustrated the home side until Amdy Faye was sent off for a two-footed tackle on Mohamed Shawky; Afonso Alves converted the resulting direct free kick.

[70] The international break left Middlesbrough without Tuncay and Shawky after both picked up injuries, while David Wheater could only make the bench after suffering from tonsillitis, so Digard, Riggott and Mido came in.

Afonso Alves smashed the ball past Paul Robinson on 74 minutes, while Marvin Emnes finally made his Premier League debut after 84.

Boro's lead didn't last long however, as Bernard Mendy's shot hit the post and rebounded off of goalkeeper Ross Turnbull to go down as an own goal.

It got worse for the visitors as just a few minutes later, Hull were awarded a soft penalty when Wheater tangled with Geovanni – a challenge which also saw the Middlesbrough defender receive a red card.

Emmanuel Adebayor put Arsenal into the lead after quarter of an hour, but Aliadière got on the end of a wonderful cross from Tuncay to head home the equaliser twelve minutes later.

Another deflection saw Robert Koren's strike roll past Ross Turnbull to put the home side two goals up early in the second half.

Both sides had chances throughout the game but City were the only one to convert – Craig Bellamy's shot across goal went between Robert Huth's legs and beyond the reach of Brad Jones into the corner of the net.

Summer departure Lee Cattermole's strong-but-fair challenge on Didier Digard forced the midfielder off with injuries to both legs that would likely rule him out for the remainder of the season.

[100] A victory in their FA Cup fifth-round replay sent Middlesbrough into the home match with Liverpool with optimism that their disastrous run of form in the league would finally come to an end, and their hopes came true.

All three vital points were secured after a defensive slip by former Boro captain George Boateng let Marlon King in to make the score 3–1.

[110] Middlesbrough's dire away form continued at the Emirates Stadium as a Cesc Fàbregas double condemned them to a 2–0 defeat, a club record tenth straight away loss.

Jérémie Aliadière had an early low shot saved by Ben Foster, but other than that failed to threaten a United side who rested several key players in preparation for their upcoming UEFA Champions League match.

Tuncay's early shot rebounded off of the Newcastle keeper and then off Habib Beye, who put the ball into his own net for an own goal, giving the visitors the lead after just three minutes.

[113] A great escape looked on the cards when Middlesbrough went a goal up at home to Aston Villa in their penultimate game of the season, courtesy of an overhead kick from Tuncay.

[115] Stewart Downing's injury kept him out of a Premier League game for the first time since November 2006, also throwing doubt on a possible summer transfer, and Tuncay captained the side.

Gareth Southgate fielded a slightly weakened side, though handed Marvin Emnes his debut, along with first starts for Justin Hoyte and Didier Digard.

Stewart Downing's first goal of the season put the visitors ahead midway through the first half, while Afonso Alves spurned several chances to extend their lead.

[121] The replay was played in front of a small but very vocal Boro crowd who were fired up by an unfortunately worded letter from the club seemingly asking them to sit down and be quiet in their last home game.

[100] The fans didn't have to wait long for a goal as in the fifth minute Stewart Downing curled an unstoppable free-kick over the wall and into the top-right hand corner of the net.

[128] On 11 August 2008 it was announced that former Manchester United youngster Ben Collett, who five years earlier had a "career-ending" injury as a result of a tackle in a game versus Middlesbrough's reserves, had been awarded more than £4.5 million in compensation.