In the first round of the 2010 FIFA World Cup qualification, El Salvador eliminated Anguilla with a 16 – 0 on aggregate and advanced to play in the Second Round against Panama and eliminated "Los Canaleros" by an aggregate score and advanced to the Third Round. He then managed to advance El Salvador to the Hexagonal which is the final qualifying round for CONCACAF. El Salvador had not qualified to the Hexagonal since the 1998 World Cup qualifying. On 14 December 2009, De los Cobos announced he would not continue as the manager of the Salvadoran national team after the end of his contract. He mentioned that one of his reasons for not renewing his contract was due to him no longer being motivated to continue on with the national team.
On 8 January 2010, it was declared that Carlos de los Cobos was the new coach for the Chicago Fire. Having missed the playoffs for just the second time in club history in 2010 and sitting near the bottom of the league with a 1–4–6 record, De Los Cobos was dismissed on 30 May 2011 and replaced by Frank Klopas. He finished with an overall record of 10–16–15 in league play and 12–18–17 across all competitions with the Fire, compiling the worst record of any coach in the club's history.