McClaren's record with Middlesbrough (reaching four semi-finals, and winning a two-legged on against Arsenal, probably make him the best English manager over the period 2003-2006. His selection was praised by numerous other commentators, including Sir Alex Ferguson and Sir Trevor Brooking. He guided Middlesbrough to winning the league cup in 2004 with victory over Bolton. McClaren's record with Middlesbrough (reaching four semi-finals, and winning a two-legged on against Arsenal, probably make him the best English manager over the period 2003-2006. His selection was praised by numerous other commentators, including Sir Alex Ferguson and Sir Trevor Brooking. He guided Middlesbrough to winning the league cup in 2004 with victory over Bolton.

In the summer of 2001, McClaren was offered the post as manager of Middlesbrough by club chairman Steve Gibson. He achieved an FA Cup semi-final place in his debut season, suffering defeat to Arsenal. He was then in charge as Middlesbrough won their first ever major honour, winning the League Cup in 2004 against Bolton Wanderers at the Millennium Stadium in Cardiff, taking them into European football for the first time and overseeing the recruitment of many big-name international footballers to the club, including ex Chelsea star Jimmy Floyd Hasselbaink. He also has pushed the club to reach their highest finish in the premier league, 7th in the 2004-05 season, which gave them another run in Europe cup competition. In the 2005-06 campaign, Middlesbrough achieved a last four place in the FA Cup and they suffered a 4-0 defeat to Sevilla of Spain in the UEFA Cup final in May 2006.

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