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The Offensive & Defensive Lob
Here are 3 keys (to both the offensive and defensive lob) for a beginner/intermediate level player:
Offensive Lob
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When to use it: This is a great stroke to use against a "serve & volley" style player or against aggressive players/teams that like to come into the net frequently, especially You have two options when opponents "crash the net" early, then just camp out at the net. They are pressuring you to make an error on one of two difficult shots: a passing shot to either side of them (or directly at their body), or an offensive lob (with topspin) over their heads. It's easier to pull off a lob when you are deeper in your own court; very little backswing is required.
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Prep: Mask your shot, as if you were preparing to hit a groundstroke winner. But then dip your racket head extra low in preparation for lifting the ball with extreme topspin.
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Contact: Swing low-to-high to lift & spin the ball just over the net player's racket reach. The ball will then speed up as it bounces out of your opponent's court.
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Follow through: End with your hands extra high with your strings still facing your opponent.
Defensive Lob
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When to use it: To stay alive! Use a defensive lob to neutralize your opponent's attack. Usually, you'll be off the court or extremely off balance. Sending your opponent a "Moonball" will buy you the time you need to get back into the point.
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Prep: Get to it plenty early. It's easy to pace yourself and think you have plenty of time to set up your shot. This is far from true, especially when playing outdoors. The wind or spin of the ball will carry it small (or great) distances away from where you anticipate the ball to eventually fall into your hitting zone. By getting there early, you will have time to compensate for these changes.
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Contact: Scoop it, lifting the ball up. Hit it DEEP to your opponent's backhand.
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Follow Thru: Recover to the center mark or a neutral location that will cut off your opponent's next shot.
How to Work a Lobber
Don't hit deep. Bring the "Lobber" off his/her game by bringing them in, uncomfortably close, with a dropshot. Then finish them off with a volley.
Lob Theory (Offensive & Defensive)
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When: Hit when your opponent is at the net.
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Where: Played from around the baseline. (Deep)
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Watch your opponent. The closer they are to the net, the more effective your lob will be.
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Grip: Same as forehand and backhand groundstrokes.
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Prep: Same as groundstroke.
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Keep your shoulders level to mask your shot.
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Contact: Out to the side and slightly in front of you. Racket face is slightly open. Weight moves from back foot to forward foot.
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Follow Through: Finish high above your shoulder before it moves across your body.
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Outcome: Push your opponent back, away from the net.
Offensive Lobbing Basics (and sweet music)
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Set up like you're going to drive the ball.
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You've got to think "SPIN" in order to lift the ball up and over the opponent's head and into the back of the court.
Basic Defensive Lob Drill Progression
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Beginner Grip: Continental (or whatever feels natural when you hit a normal one-handed or two-handed groundstroke).
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Swing: Racket face is open and path of racket moves from beneath the ball to following through above the head. (It can move across your body naturally after you've learned these fundamentals.)