Ross Benjamin Ross Benjamin
Monday MLB Underdog Winner ready to cash! MLB Picks 19-11 (65%) L30 includes 9 MLB underdog winners. Since 2012, NHL Playoff Picks are 145-99 (59%). All 10* Top Plays 57-38 (60%) L95 & 35-20 (63%) L55.
3 days All Sports subscription of Ross Benjamin

With this subscription you'll get every single play released for 3 consecutive days! This is our most popular subscription during football season because it gets you all of Saturday and Sunday's picks PLUS any plays on Monday Night Football! 

No picks available.

7 days All Sports subscription of Ross Benjamin

Looking for some great value? Pick up a weekly package and get SEVEN DAYS full days of picks! It's easy to see why this is one of the most popular choices on the site. 

No picks available.

30 days All Sports subscription of Ross Benjamin

SAVE A TON of money with a 30 Day subscription! You'll literally pay a fraction of the cost by signing up for a full month instead of making a single purchase each day! 

No picks available.

90 days All Sports subscription of Ross Benjamin

This package gets you three months (90 Days) of all picks in all sports! 

No picks available.

180 days All Sports subscription of Ross Benjamin

This package gets you every play in every sport for a full 6 months! The ultimate package for maximum action and the biggest winners in the industry! 

No picks available.

365 days All Sports subscription of Ross Benjamin

You'll learn how the pros make a living via sports betting with EVERY PLAY released over the next 365 days. 

No picks available.

2018 NHL Stanley Cup Playoffs
**4x Top 10 NHL handicapper!**

Currently on a 18-14 NHL run since 04/12/18.

This subscription includes EVERY NHL PREMIUM PICK I release through the end of the Stanley Cup! Join now and start cashing in on more winners!

No picks available.

NBA Season Subscription
1-0 run in NBA dating back to 05/21/18.

This subscription includes EVERY NBA PREMIUM PICK I release through the end of the NBA Finals! Join now and start cashing in on more winners!

No picks available.

MLB Playoff Subscription
**2x Top 10 MLB handicapper!**

$1,000/game players have cashed in $10,810 on my MLB picks since 04/21/18!

This subscription includes EVERY MLB PREMIUM PICK I release through the end of the World Series! Join now and start cashing in on more winners!

No picks available.

Matchup Selection W/L
MLB  |  May 21, 2018
Yankees vs Rangers
OVER 9½ -103 Won
Play Type: Free

Ross Benjamin has a NBA, MLB, and NHL winners on Monday’s card that are up for sale and ready to cash! Since 2012, Ross is 145-99 (59%) with his NHL Stanley Cup Playoff picks and those 244 selections came at an average money line price of -106. Additionally, Ross is a stellar 19-11 (63%) L30  with his MLB picks and that includes 9 money line underdog winners.

Yankees (Tanaka) @ Rangers (Colon) 8:05 PM ET

Game# 961-962

Play On: Over 9.5

Masahiro Tanaka has made 2 career starts at Texas and posted a large 9.90 ERA and 2.20 WHIP during these outings. Furthermore, Tanaka has seen each of his previous 6 outings go over the total. His pitching adversary will be 45-year-old Bartolo Colon who’s enjoying a great beginning to 2018. However, Colon made 2 starts against the Yankees last year and compiled a massive 12.28 ERA. Colon has also allowed 6 home runs at home this season in just 17 2/3 innings pitched. Texas is 45-22 (67.2%) over the total at home during the past 2 seasons when facing a team with a winning record. The Rangers enter today with a poor season record of 18-30 (.375). The Yankees are 11-2 (84.6%) over the total this season when facing a team with a win percentage of .380 or less. Bet on this game to go over the total for a 5* wager.

Matchup Selection W/L
NBA  |  May 21, 2018
Celtics vs Cavs
-7 -104 at pinnacle
Play Type: Premium

Boston @ Cleveland 8:35 PM ET

Game# 705-706

Play On: Cleveland -7.0 (5*)

Boston is a very talented young team with an extremely bright future. It’s even more impressive what they’ve accomplished to reach this far after losing star point guard Kyrie Irving late in the season due to a knee injury. However, winning on the road in the playoffs has been a struggle for this youthful bunch. Despite Boston leading this Eastern Conference Finals series and being 2 wins away from advancing to the NBA Finals, they’ve gone 1-5 on the road during postseason action. Cleveland won Game 3 by a decisive 30-point margin and regained their confidence after sustaining a pair of double-digit losses at TD Garden in Boston.

Any favorite (Cleveland) of 3.5 to 9.5 points coming off a home win by 20 points or more, and they’re facing an opponent (Boston) coming off a road loss by 10 points or more, resulted in those favorites going 33-11 ATS (75%) during the past 5 seasons. Bet on Cleveland minus the points for a 5* wager.

Matchup Selection W/L
NHL  |  May 21, 2018
Lightning vs Capitals
+109 at betonline
Play Type: Premium

Tampa Bay @ Washington 8:05 PM ET

Game# 9-10

Play On: Tampa Bay +109 (5*)

Washington is going through another one of their postseason choke jobs. After winning the first 2 games of this series on enemy ice, and seemingly being in total control, they’ve preceded to lose 3 straight and now find themselves on the brink of elimination. The bottom line is this, Tampa Bay’s Andrei Vasilevskiy has thoroughly outplayed Washington’s Braden Holtby over the past 3 games. During that stretch, Holtby has an awful .843 save percentage, and Vasilevskiy’s is a stellar .943. Additionally, Tampa Bay has won 5 straight road games this postseason while Washington has gone 3-5 at home. Bet on Tampa Bay for a 5* money line underdog wager.

Matchup Selection W/L
MLB  |  May 21, 2018
Diamondbacks vs Brewers
+103 at betonline
Play Type: Premium

Arizona (Greinke) @ Milwaukee (Anderson) 7:40 PM ET

Game# 957-958

Play On: Milwaukee +103 (5*)

Zack Greinke has struggled in 3 road starts this season which is evidenced by his hefty 7.27 ERA during those outings. Greinke has made 4 career starts at Milwaukee and posted an uninspiring 4.73 ERA during those outings. The Diamondbacks have gone a dismal 1-10 during their last 11 games and have scored 2 runs or less in 8 of its previous 10 outings. Arizona will be facing Milwaukee starter Chase Anderson on Monday. The Brewers right-handed hurler has collected a stellar 1.15 WHIP in 8 starts this season. Meanwhile, Arizona has gone 3-14 in 2018 when facing a National League starting pitcher with a WHIP of 1.25 or less.

Milwaukee is coming off yesterday’s 3-1 loss at Minnesota. The Brewers are a perfect 6-0 in their last 6 games following a loss. Milwaukee will be facing an Arizona team today that’s gone 17-4 this season against teams that average 2.75 or less extra base hits per game. Bet on Milwaukee for a 5* money line wager.


Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators over the last 15 years. 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 60 years old and has been directly involved in many capacities of the sports gaming industry for the last 31 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        


Ross the Writer @ Sportsbook Review

Writer/Video Analyst of 2424 articles and over 950 correlating videos.



Host of The Ross Benjamin Show: From 09/12 to 03/13 on Sports Talk Radio 1280

Host of Winning Sports Advice in 2012

Host of Ross Benjamin Show on Sports Journey Network from April,2009 to July, 2010

Host of Phoenix Sports Ticket in 2006


Recent Guest Radio Appearances

Tony George Show in 2014 and 2015 on Yahoo Sports Radio and the Armed Forces Network


Additional Guest Appearances since 2007

KFNS AM 590 "The Fan"-St. Louis, Missour

iWAXY AM 790 ESPN- Miami, Florida

WHBQ AM 560- Memphis, Tennessee

WHTK AM 1280- Rochester, New York

WJOX AM 690- Birmingham. Alabama

KTIK AM 1350 ESPN-Boise, Idaho

WJDX AM 620-Jackson, Mississippi

CKST AM 1040-Vancouver, British Columbia

KTKR AM 760 "The Ticket"-San Antonio, Texas

KZNS AM 1280 "The Zone" Salt Lake City, Utah  



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