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Baseball Handicapping Guide

Written by Jimmy Boyd

This baseball handicapping guide is going to show you how you can use a few simple strategies to increase your chances of winning when betting on MLB games. It isn’t going to get much easier than this unless you want to skip doing it on your own and get signed up for our premium baseball picks, which win and win big year in and year out. 


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The strategy that we are going to talk about today has three easy steps:

1. Bet on the two best teams in the league for the last three months of the season.

2. Do your baseball betting on these teams using a two-team parlay.

3. Be consistent with your betting every day for a month at a time.

Let’s take a look at how this system did during the month of June at beating the MLB betting lines, and we will also use those results as an example on how this easy to use method works in practice. 

We have talked about how in baseball you want to bet underdogs and taking favorites is a big mistake. It puts too much of your bankroll at stake for each game and you can start chipping away at your money quickly if you don’t stay away from the big favorites (-180 and above). 

Let’s take a look at the two best teams in baseball, the Boston Red Sox and the Chicago Cubs. Right now these teams have the best record in baseball and even though they are heavy favorites almost every single day, especially if they are at home, you can profit on them if you add a kink to the equation and parlay these two teams together.

Now we know that simple-minded sports handicappers will tell you to avoid parlay wagers at all costs, and we think that is good advice for the most part, but like anything in life there isn’t just black and white but a little bit of a grey area. We think parlaying high favorites in baseball is perfectly ok, just like parlay the side and total of a football or basketball game can give you an edge. 

So our baseball betting system works like this:

Every day, and we mean keep it consistent and do it everyday, you parlay the Red Sox and Cubs to win. Even if one or both of the teams are heavy favorites you should still get underdog value on your parlay. It is approximately even money when both teams are -240 favorites, (i.e. bet 100 to win 100), which is going to be rare. Below I have some payouts based on a $100 parlay bet. You can see what various payouts would be with different betting lines.

Team A Team B Payout

-110 -110 +264
-120 -120 +236
-130 -130 +213
-140 -140 +193
-150 -150 +177
-160 -160 +164
-170 -170 +152
-180 -180 +141
-190 -190 +132
-200 -200 +125

As you can see, even if both teams are middle level favorites then it’s still like you are betting a decent underdog. Now both teams have to win in order for you to cash your bet, but since you are taking the best two teams in baseball that should be too much of a problem.

Below you will see how this system worked in the month of June with the Red Sox and Cubs.

Boston Red Sox
18 – 7 Record in June 72%
62-36 Record as of July 26 63%

Chicago Cubs
19 – 9 Record in June 68%
63 – 36 Record as of July 26 64%

Parlay Betting System
10 – 14 Record in June 42%
10 parlay wins = $2026
14 parlay loses = -$1400

Profit = $626
(Based on $100 bets)

Longest losing streak – 3 parlay bets
Longest winning streak – 4 parlay bets

As you can see above, for the month of June this system proved to be very profitable. It went 10-14, but the profit was roughly $600 dollars, not to bad for placing the same exact bet over and over for one month.

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