Town went down 2-0 to Middlesbrough at the Riverside Stadium, thanks to a goal in each half from Luke Williams and Mustapha Carayol.
Blues did have chances of their own which they failed to take and despite an encouraging display, left the North East with nothing to show for their troubles.
Paul Jewell handed a Town debut to midfielder Guirane N’Daw in place of Massimo Luongo, with the Spurs loanee dropping to the bench.
Captain Carlos Edwards also returned to the starting line-up, replacing Jack Ainsley at right-back.
The first chance of the game fell to the home side after nine minutes, with a neat through ball releasing Ishmael Miller clean through on goal but he was thwarted by a superb stop from Scott Loach, who raced off his line to deny the striker.
Town reacted to this early effort well and a fine pass from Edwards sent Taylor through but the striker fired his effort just wide of Jason Steele’s near post after ten minutes.
More good work from Town saw Blues go close once again three minutes later, as Drury played in Martin, who then cut inside George Friend before seeing his effort tipped over the bar by Boro ‘keeper Steele.
Taylor was at the heart of every move for Town and the former Peterborough man went close twice for Blues midway through the first-half.
First he saw a long range effort fly just over the bar after 18 minutes, before then seeing an audacious lob from out wide tipped over the bar by a back-pedalling Steele nine minutes later.
From the resulting Drury corner, Steele had to be alert to hold on to a Tommy Smith goal-bound header.
Despite Town’s first-half dominance, Paul Jewell’s side found themselves behind 11 minutes before the break.
Drury was robbed in possession of the ball by Josh McEachran and he immediately fed Williams who emphatically finished past Loach and into the bottom corner to open the scoring.
Town did have a chance to equalise four minutes before half-time though, as the lively Taylor danced past a couple of Boro defenders and into the penalty area before firing in a shot that whistle just past the post with Steele well beaten.
But that was the way it stayed as the referee soon blew for half-time, meaning Williams’ strike was the difference as Blues went in behind at the break.
The hosts had a chance to double the lead 30 seconds after the restart, but Loach was alert to beat away an Adam Reach shot.
Substitute Lukas Jutkiewicz then went close for Boro on the hour mark, firing just wide of Loach’s near post.
Former Town man Grant Leadbitter was next to test Loach, with a rasping drive from range that the Blues stopper was happy to watch sail over his bar.
Town did create a good opening after 65 minutes though, with Taylor playing in strike partner Chopra, but the latter’s effort was turned behind for a corner by Steele.
With 16 minutes left on the clock, Taylor tried his luck from just outside the area but dragged his shot wide of Steele’s post.
Taylor went close again for Town with nine minutes remaining, after receiving a lay-off from Lee Martin, but the striker fizzed his shot just wide of the upright and behind for a goal-kick.
More good passing from Town saw Luongo and Taylor play a neat one-two, with the latter then firing in a shot that flashed just wide of the target with six minutes left on the clock.
But Town were punished by the hosts in injury as Blues were caught on the break looking for an equaliser. Steele punted the ball up the pitch to Carayol, who coolly slotted past Loach and double Middlesbrough’s lead.
The referee soon blew for full time and Town will now focus their attention to Wednesday’s date with Wolves at Portman Road.
Middlesbrough: Steele, Hoyte, Woodgate, Bikey, Friend, Reach, Leadbitter, McEachran, Thomson (Zemmama 85), Williams (Carayol 70), Miller (Jutkiewicz 56). Subs not used: Leuitwiler, Hines, Arca, Ledesma.
Town: Loach, Edwards, Chambers, Smith, Cresswell, Drury (Luongo 72), N’Daw, Taylor, Martin, Murphy (Scotland 79), Chopra (Emmanuel-Thomas 85). Subs not used: Lee-Barrett, Ainsley, Hyam, Emmanuel-Thomas, Murray.
Att: 14,887 (390 Town fans)