- June 12, 2005– ROH: The Masked Boston Superstar vs. Derek Dempsey ended in a NO CONTEST when Shane Douglas showed up!
- July 23, 2005–Ring of Honor: Shane Hagadorn & Matt Turner defeated Derrick & Bobby Dempsy..
- July 30, 2005–IWA Mid South: Delirious & Matt Sydal defeated Derrick Dempsey & Davey Andrews..
- September 24, 2005–Ring of Honor: Shane Hagadorn & Devito defeated Derrick Dempsey & Kelly Primo..
- November 4, 2005–ROH: Davey Andrews beat Derrick Dempsey & Shane Hagadorn in a 3-WAY to win the Top of the Class Trophy..
- November 5, 2005–Ring of Honor: Derrick Dempsey & Bobby Dempsey defeated Brad Bradley & Darren Wade..
- November 11, 2005–Full Impact Pro: Steve Madison defeated Derrick Dempsey..
- January 14, 2006–ROH: Derrick Dempsey beat Shane Hagadorn and Pelle Primeau and Smash Bradley in a 4-WAY…
- February 25, 2006–Ring of Honor: Derrick Dempsey & Rick Titus defeated Jason King & Smash Bradley..
- March 11, 2006–Ring of Honor: Derrick Dempsey & Bobby Dempsey defeated Shane Hagadorn & Pelle Primeau..
- April 22, 2006–Ring of Honor: Derrick Dempsey defeated Pelle Primeau..
- May 12, 2006–ROH: Pelle Primeau beat Derrick Dempsey and Shane Hagadorn & Mitch Franklin in a 4-WAY Elimination Match..
- June 3, 2006–Ring of Honor: Shane Hagadorn defeated Derrick Dempsey by Submission to win the Top of the Class Trophy..
- August 5, 2006–Ring of Honor: Derrick Dempsey defeated Pelle Primeau..