Ross Benjamin Sports


Ross Benjamin Sports
Ross Benjamin Sports

Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators over the last 15 years. Included in professional sports handicapper Ron Raymond’s 2008 published book “50 Greatest Sports Betting Secrets” he probably says it best. “One of the most underrated handicappers in our industry and probably one of the sharpest ones I know is Ross Benjamin.”

One of Ross’ often used phrases when speaking publicly, “if you want to be a successful sports handicapper then start by thinking like a bookmaker”. Ross is now 62 years old and has been directly involved in many capacities of the sports gaming industry for the last 35 years. However there is nothing he enjoys more than the challenge of picking winners in the NFL, NBA, MLB, NHL, NCAA Football, and NCAA Basketball.

Sports Handicapping Achievements

Playbook Wise Guy Invitational Contest

  • 4th Place-2015 (50 contestants)-Prize: $666.00
  • 5th Place-2013 (50 contestants)-Prize: $333.00
  • 1st Place-2003 (73 contestants)-Prize: $10,700

Sports Watch

  • #1-2010-2011 NCAA Basketball Regular Season: 116-77 (60.1%)
  • #6-2011 March Madness- 28-21 (57.1%)

Oklahoma Sports Monitor

  • #1-2008 March Madness: 29-17 (63%)
  • #1-2007 NFL Playoffs in Net Profit: 9-2 (81.8%)

Big Guy Sports Monitor

  • #1-NHL 2005-2006 Season

  • #1-2003 College Football Season:  45-23 (66.2%)

Annual Rankings at

  • #7-2015 MLB Season
  • #3-2014/2015 NHL Season
  • #6-2012 NFL Preseason
  • #7-2011/2012 NHL Season
  • #8-2011 NFL Season
  • #2-2011 NFL Preseason
  • #9-2010 NFL Season