This study examines the extent to which two civil libertarian interveners, the Canadian Civil Liberties Association (CCLA) and the British Columbia Civil Liberties Association (BCCLA), have been successful at achieving favourable policy outcomes through Supreme Court of Canada decisions. Cases directly and indirectly implicating fundamental freedoms under section 2 of the Charter of Rights were the focal point. The selected timeframe for this study was 1999-2009 and a total of thirteen cases in which the CCLA and/or the BCCLA intervened constitute the data set. Four of the cases invoke Charter section 2(a) (“freedom of religion”) and nine invoke Charter section 2(b) (“freedom of expression).” Methodologies highlighting the legal issues at trial and those that considered how the litigation will influence a policy status quo were synthesized to accomplish this goal. Analysis of these cases reveals that civil libertarians were more likely to emerge victorious in common law as opposed to constitutional cases. Constraints imposed by “reasonable limits” under section 1 of the Charter and the presence of governments as direct parties proved to be a barrier to the success of civil libertarians in court. This explanation offered complements a finding in the literature that governments are the most successful “Repeat Player” in court.