The purpose of the double cutoff is to provide an easier target for an outfielder on a long throw from the gap or down the line. On these hits the outfielder is in the deepest part of the field and is trying to throw the ball as hard as he can to get it in quickly. Since he is unable to come in on the ball and gain momentum, this throw will often not be as accurate. By providing two infielders spaced apart, your team will have a better opportunity of having a successful relay.
The way you handle cutoffs from the outfield will vary depending on age and skill level. The following pages have a number of diagrams of how you can handle double cutoffs at the youth level.
Many coaches continually yell out to the outfield during the game, "Hit the cutoff man", "Make sure you hit the cutoff", "Why didn't you hit the cutoff?". But, unless you practice plays which require a decision to be made during practice, your outfielders may not really understand why it's important. During practice don't always have the ball go through to the base. Have your players use "Cut" followed by a different base.
As with a single cutoff situation, don't overlook the positioning of the infielders as they get into position. You want the outfielder to make the longer throw and the infielder to make the shorter throw. If an outfielder is continually overthrowing both cutoff men in practice then chances are they are going to far out.
You can often take advantage of an aggressive baserunner that isn't as careful as he should be. A stand up double is an example where an aggressive baserunner can provide you with an easy out.
This play is most effective when the ball is hit to the either left-center or right-center.
The shortstop and second baseman will go out for a double cut lining up as usual towards third base.
The first baseman will stay in his position until the runner has passed by. Then the first baseman should start trailing the runner towards second base. The first baseman should try to time his arrival at second, so a quick throw from one of the cutoff men to second will meet him at the bag. This means the first baseman must be aware of where the ball is, not just following a certain number of feet behind the runner. The goal of the first baseman is to sneak in behind the runner without the runner or third base coach noticing.
The third baseman has the call on the play. If he sees the runner take a turn at second but not continue on to third, he can call "cut", the shortstop and second baseman need to be trained to quickly look to second when they get the cut call from the third baseman. You don't want the third baseman to yell, "cut - two", or a player that is unaware that the first baseman is there, will no know to get back quickly.