FC, missing scoring a goal line ball that would have taken Toronto to the CONCACAF Champions League. After the match, TFC coach John Carver said "I am thinking, ‘How did he score 99 goals?’ That’s what I thought.’" On August 8, 2008, Cunningham was traded to FC Dallas in exchange for a third-round pick in the 2009 MLS SuperDraft. He scored in his first match with FC Dallas on August 16, 2008 in a 2–1 loss to the Columbus Crew. It was Cunningham's 100th goal in MLS. Jeff played in 11 games with FC Dallas during the 2008 season scoring 5 goals. Cunningham scored 17 goals in 2009, including four goals on August 1 against the Kansas City Wizards. After Kenny Cooper left the club for 1860 Munich, Cunningham emerged as the team's go-to goal scorer. He netted seven goals in five games in September, winning MLS Player of the Month and went on to win the 2009 MLS Golden Boot. Cunningham ended the 2010 season as the #2 career regular season MLS goalscorer with 132 goals. After the 2010 MLS season FC Dallas declined Cunningham's contract option and Cunningham elected to participate in the 2010 MLS Re-Entry Draft. On December 15, 2010 Cunningham was selected by Columbus Crew in Stage 2 of the Re-Entry draft. Prior to Columbus re-signing him on January 28, 2011, Cunningham trained with Norwegian Premier League club IK Start and was rumored to be in talks for a permanent move, however no trade came to pass. His return to Columbus Crew was on February 22, 2011 in the second half of the Crew's CONCACAF Champions League quarter final game against Real Salt Lake. On July 7, 2011, Cunningham scored his 133rd career MLS Goal to tie the MLS All-Time Scoring Record. The goal came in the 90th minute on a header to win a game against the Vancouver Whitecaps FC by a score of 1–0. On August 27, 2011, Cunningham scored his 134th career goal, making him the all-time leader in MLS soccer in a 6–2 loss to the Seattle Sounders. At season's end, Columbus declined his 2012 contract option and he entered the 2011 MLS Re-Entry Draft. Cunningham was not selected in the draft and became a free agent. In January 2012, Cunningham signed on with first division side and current runner up CSD Comunicaciones of Guatemala for the 2012 Torneo Clausura. After his