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Ross Benjamin

Ross Benjamin

Hot Streaks

NBA Postseason Wagers: 139-100 (58.2%) & +11,315 since 2022.

NBA Postseason Sides: 78-48 (61.9%) & +8930 since 2023.

58-27 (68.2%) & +7916 since Mar 16, 2021 in NBA Money Line Wagers

NBA 5% Best Bets: 39-24 (61.9%) & +6085 since Apr 8, 2021 in NBA

13-4 (76.5%) & +2616 since May 12, 2025 on all MLB Wagers

17-8 (68%) & +2648 since May 13, 2025 in All Sports

Last updated May 22, 9:39 AM EDT

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Last 20

Date
Sport
Pick
Result
May 22
NBA
3% – Minnesota Timberwolves +7.5 (-112)
(Analysis)
Loss
May 21
NBA
3% – Indiana Pacers +4.5 (-110)
(Analysis)
Win
May 21
MLB
2% – Boston Red Sox -139 T Megill (RHP), G Crochet (LHP) Must Start
(Analysis)
Loss
May 20
MLB
3% – St. Louis Cardinals +1.5 (-113) T Skubal (LHP), E Fedde (RHP) Must Start
(Analysis)
Win
May 20
MLB
3% – (921) New York Mets at (922) Boston Red Sox Total Under 8.5 (-108) C Holmes (RHP), W Buehler (RHP) Must Start
(Analysis)
Win
May 20
MLB
3% – (903) Cincinnati Reds at (904) Pittsburgh Pirates Total Under 8.0 (-118) N Martinez (RHP), B Falter (LHP) Must Start
(Analysis)
Win
May 20
NBA
3% – (527) Minnesota Timberwolves at (528) Oklahoma City Thunder Total Under 215.5 (-110)
(Analysis)
Win
May 19
MLB
4% – (973) Kansas City Royals at (974) San Francisco Giants Total Under 7.5 (-113) K Bubic (LHP), R Ray (LHP) Must Start
(Analysis)
Win
May 19
MLB
3% – (951) Cincinnati Reds at (952) Pittsburgh Pirates Pittsburgh Pirates Total Under 3.5 (-105) N Lodolo (LHP), M Keller (RHP) Must Start
(Analysis)
Win
May 18
NBA
3% – Oklahoma City Thunder -8.0 (-110)
(Analysis)
Win
May 18
NHL
2% – (27) Florida Panthers at (28) Toronto Maple Leafs Total Under 5.5 (-145)
(Analysis)
Loss
May 17
MLB
4% – St. Louis Cardinals +105 M Mikolas (RHP), Undecided (LHP) Must Start
(Analysis)
Win
May 17
NHL
3% – (23) Winnipeg Jets at (24) Dallas Stars Total Over 5.5 (-110)
(Analysis)
Loss
May 16
MLB
3% – (923) Minnesota Twins at (924) Milwaukee Brewers Total Under 7.5 (-108) J Ryan (RHP), C Patrick (RHP) Must Start
(Analysis)
Win
May 16
MLB
3% – (917) Atlanta Braves at (918) Boston Red Sox Total Under 8.0 (-118) C Sale (LHP), G Crochet (LHP) Must Start
(Analysis)
Win
May 16
MLB
3% – (929) Athletics at (930) San Francisco Giants 1H Total Under 3.5 (+100) J Sears (LHP), L Webb (RHP) Must Start
(Analysis)
Loss
May 16
NBA
3% – Boston Celtics +2.5 (-108)
(Analysis)
Loss
May 16
MLB
3% – (907) Houston Astros at (908) Texas Rangers Houston Astros Total Under 3.5 (-135) L Mccullers Jr (RHP), N Eovaldi (RHP) Must Start
(Analysis)
Loss
May 15
MLB
2% – (961) Athletics at (962) Los Angeles Dodgers Total Over 10.0 (-103) O Bido (RHP), M Sauer (RHP) Must Start
(Analysis)
Win
May 15
MLB
3% – (957) Houston Astros at (958) Texas Rangers Total Under 7.0 (-108) H Brown (RHP), J Degrom (RHP) Must Start
(Analysis)
Win
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Consultant Bio

Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators over the last 21 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 and sharpest sports handicappers I know is Ross Benjamin.

Ross’s sports betting advice is simple yet prophetic. If you want to be a successful sports handicapper, then start by thinking like an oddsmaker.
 

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