Massimo Maccarone's two late goals earned Middlesbrough a 2-0 win over Litex Lovech.
Two late goals from Massimo Maccarone earned Middlesbrough a laboured 2-0 win over Litex Lovech to ensure they finished top of Group D in the Uefa Cup.The Italian struck twice in the last ten minutes to give Steve McClaren's men the three points and top spot in the group.
Maccarone broke the deadlock on 80 minutes and followed that up with a brilliant strike six minutes later to finally see off the stubborn Bulgarians.
Middlesbrough began brightly with Adam Johnson causing panic in the very first minute with a strong run down the left and his cross was fumbled by Vitomir Vutov, but the goalkeeper recovered to snatch the ball off the toes of Jason Kennedy.
Johnson was enjoying a productive start to the game and he fashioned a chance for himself on four minutes and his powerful shot from the edge of the area was pushed out by Vutov.
Maccarone wasted an opening to score on 12 minutes when Jimmy Floyd Hasselbaink played him in on goal, but the Italian could only fire his shot straight at Vutov.
Franck Queudrue had the next chance for Middlesbrough on 16 minutes when he headed Johnson's corner wide of the target.
Litex came close to breaking the deadlock on 21 minutes when Mihail Venkov beat Matthew Bates to the ball down the left before cutting it back for the onrushing Milivoje Novakovic, who fizzed his shot just past the post.
The home side created another opening a minute later when Hasselbaink teed up Kennedy for an acrobatic volley which flew just over the crossbar.
Litex midfielder Petar Zlatinov almost caught out Boro goalkeeper Brad Jones close to the half-hour mark with a long-range shot, which the Australian was forced to tip over the crossbar at full stretch.
Middlesbrough had claims for a penalty turned down on 53 minutes when Hasselbaink went down under a challenge Todor Palankov, but much to the Dutchman's frustration, the foul was adjudged to have occurred on the edge of the box.
Jones had to be alert on 56 minutes when he was forced to rush from his goal to deny Novakovic getting through and two minutes later, Novakovic saw a powerful volley kept out by Jones, as Litex grew in confidence.
Maccarone should have opened the scoring on 61 minutes when Queudrue headed Kennedy's corner down into the path of the Italian right in front of goal, but his first touch let him down and Vutov was able to clear the danger.
Just when it looked like Middlesbrough were running out of ideas to breakdown the Litex defence, the home side broke the deadlock ten minutes from time when Johnson weaved his way past a couple of challenges and sent over an inviting cross for Maccarone to head home at the back post.
Maccarone made the game safe on 86 minutes when he picked up the ball midway inside the Litex half and ran forward before unleashing a superb left-footed shot into the top corner to bring the crowd to its feet.
Litex secured their place in Friday's draw by finishing in third in Group D, despite losing at The Riverside Stadium.
In the other Group D contest on Thursday evening, a second half goal from Danny Koevermans gave Dutch Eredivisie high-flyers AZ Alkmaar a 1-0 win over Swiss side Grasshoppers Zurich.
| Middlesbrough | Team Statistics | Litex Lovech |
| 2 | Goals | 0 |
| 0 | 1st Half Goals | 0 |
| 4 | Shots on Target | 1 |
| 6 | Shots off Target | 10 |
| 1 | Blocked Shots | 3 |
| 6 | Corners | 4 |
| 16 | Fouls | 9 |
| 2 | Offsides | 4 |
| 1 | Yellow Cards | 2 |
| 0 | Red Cards | 0 |
| 71.8 | Passing Success | 76.8 |
| 18 | Tackles | 21 |
| 83.3 | Tackles Success | 61.9 |
| 50.5 | Possession | 49.5 |
| 55.1 | Territorial Advantage | 44.9 |
