Ankle problems again sidelined Olsen for the beginning of the 2008 MLS season, and there was speculation that his career was in jeopardy. Despite said problems, Ben Olsen was able to make one MLS appearance against the Los Angeles Galaxy on June 28, 2008. The crowd greeted him with the loudest ovation of the day and a tifo that read "Ben Olsen" and "Heart Of A Lion". After playing just 15 minutes Olsen responded to the media by stating, "It wasn't great; I was like a wounded animal out there." On July 7, 2008 Olsen underwent another ankle surgery.