Call Ross Direct At 781-571-0299

Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators over the last 17 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 63 years old and has been directly involved in many capacities of the sports betting industry for the last 35 years. He currently is a sports betting writer and video analyst for OSGA. Ross also is a regular guest on the "Raymond Report Sports Betting Podcast". 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        


Ross the Writer

  • Current writer/video analyst for the Offshore Gaming Association
  • ​Former writer/video analyst for Sportsbook Review from 2011 to 2017


  • Former sports betting analyst on the Bob Mathews Show on WHAM 1180 AM in Rochester, New York every Thursday night during the 2018-2019 and 2019-2020 football seasons.
  • Weekly guest on the Sam and Brad Show on WAKR 1590 AM in Akron, Ohio during the 2018-2019 and 2019-2020 football seasons.
  • Frequent guest on the Tony George Show in 2014 and 2015 on Yahoo Sports Radio and the Armed Forces Network.
  • Host of The Ross Benjamin Show: From 09/12 to 03/13 on Sports Talk Radio 1280 AM WHTK in Rochester, New York (current call letters are Fox Sports AM 1280)                    
  • Host of Winning Sports Advice in 2012 on Blog Talk Radio.
  • Host of Ross Benjamin Show on Sports Journey Network from April,2009 to July, 2010
  • Host of Phoenix Sports Ticket Radio Show in 2006​


Additional Guest Appearances since 2007

  • KFNS AM 590 "The Fan"-St. Louis, Missouri
  • WAXY AM 790 ESPN- Miami, Florida
  • WHBQ AM 560- Memphis, Tennessee
  • WHTK AM 1280- Rochester, New York (Friday drive time hour)
  • WJOX AM 690- Birmingham. Alabama
  • KTIK AM 1350 ESPN-Boise, Idaho
  • WJDX AM 620-Jackson, Mississippi
  • CKST AM 1040-Vancouver, British Columbia (aired during the Jim Rome Show)
  • KTKR AM 760 "The Ticket"-San Antonio, Texas
  • KZNS AM 1280 "The Zone" Salt Lake City, Utah  


  • Locker Room Picks Show (Pilot-2013) hosted by Jennifer X. Williams
  • Network: CBS Sports