Antonio Guayre opened the scoring in the 37th minute and, as Middlesbrough committed more men forward in search of an equaliser, Javi Venta added a clinching second 15 minutes from time. The win left the Spanish club, semi-finalists in this competition last season, on four points, two behind their Premiership opponents and with a game in hand. Villarreal visit FK Partizan next week and finish with a home game against point-less Egaleo FC. Middlesbrough have only Partizan to play, on 15 December, but are still well-placed to progress having won their first two games.
 A point would have been enough to send Middlesbrough into the knockout stages, although manager Steve McClaren took the opportunity to rest a number of players, including first-choice strikers Jimmy Floyd Hasselbaink and Mark Viduka. Villarreal were without José Mari Romero, who scored the goal that earned a point away to S.S. Lazio on Matchday 1 before being sent off.
 The visitors got their tackles in early and made life difficult for the home team in the opening minutes. Stewart Downing, Middlesbrough's promising young left-winger, got away for the game's first real chance but with the ball on his weaker right foot his shot failed to really test José Manuel Reina.
 Gradually Villarreal began to announce themselves and the Argentinian playmaker Juan Román Riquelme was warming to the challenge. When he bent a free-kick around the defensive wall in the 33rd minute, Mark Schwarzer first made the stop with his left hand before clearing the ball to safety with his left boot.
 The goalkeeper was forced into another save moments later and the first goal did not appear far away. It duly arrived in the 37th minute when Guayre fastened on to a through-ball from Riquelme, escaped the attentions of Chris Riggott and angled a fine finish beyond Schwarzer.
 Middlesbrough manager McClaren was intent on securing his team's qualification sooner rather than later and at the interval he brought on both his first-choice forwards. Some neat combination between Hasselbaink and Viduka immediately posed Villarreal new problems and the lead looked incrasingly fragile.
 In the 68th minute Middlesbrough had the ball in the net through Riggott after Boudewijn Zenden had nodded back a free-kick, but the defender had strayed fractionally offside. The home side expertly exploted the extra space Middlesbrough's pressure left at the back to wrap up the win in the 75th minute, Venta collecting another sweet pass from Riquelme ahead of Franck Queudrue, and lifting the ball over the helpless Schwarzer to seal the points.