Tweener Shots Ranked: Which Era Gave Us the Best Between-the-Legs Magic?

There is a sound a crowd makes when a player turns their back to the net, spreads their legs, and flicks the ball over their own head toward an opponent they cannot see. It starts as a gasp, becomes a roar, and ends in disbelief. Tweener shots — the between-the-legs trick that turns a lost cause into the highlight of the night — are the rare thing in tennis that even people who do not follow tennis will stop and rewatch. We have watched hundreds of them. We wanted to know, honestly, which era of the sport produced the best ones.

Not the most. The best. Those are different questions, and the difference is the whole piece.

What we are actually comparing

A tweener is hit between the legs, usually while running backward, usually because lobbing the player has been beaten and the only other option is to let the ball bounce twice. Most are defensive scrambles. A few are showing off. Once in a great while one wins a point that mattered, and those are the ones that live forever.

Rather than rank twenty clips in a row, we split the modern history of the shot into three eras and judged each on the same four criteria:

• Difficulty — how hard the actual shot was, given footing, ball height, and whether the player could see the court.
• Stakes — the score, the round, the tournament. A tweener at 40-love in a first round is not a tweener at match point in a major.
• Crowd payoff — the size and length of the reaction, and whether the opponent reacted too.
• Conversion — did it win the point, or just delay the inevitable in style?

That last one matters more than fans admit. A gorgeous tweener that floats long is a blooper, not a winner. We weighted conversion heavily because a trick shot you lose the point on is theater, and we wanted to separate theater from tennis.

The three eras: the Novelty Years (roughly the 1990s into the early 2000s), the Golden Age (the mid-2000s through the mid-2010s, defined by the big four), and the Showman Era (the late 2010s to now, defined by Kyrgios, Alcaraz, and a generation raised on highlight reels). We are not claiming hard boundaries. We are claiming a useful way to argue.

Era one: the Novelty Years

In the 1990s the tweener was something close to a stunt. Players hit them, but the shot carried a faint whiff of disrespect — a thing you did when you had already given up on the point and decided to entertain yourself. Guillermo Vilas is often credited with popularizing it in the late 1970s, and the move was sometimes called a "Gran Willy" in his honor in parts of South America. By the time Sampras and Agassi were trading Grand Slams, the between-the-legs shot was known but uncommon, and almost never the centerpiece of a match.

Here is the honest assessment of that era against our criteria.

Difficulty was high, but for a boring reason: the technique was less refined and the strings were less forgiving. Players hit these with natural gut or early synthetics in heavier frames, and getting clean contact while running backward was genuinely a coin flip. That makes the successful ones impressive and the failed ones numerous.

Stakes were almost always low. The shot's social role in the era was the giveaway. You attempted a tweener when the point was lost, so by definition it rarely arrived at a moment that decided anything. We struggled to find a single era-defining tweener from the 1990s that occurred at break point or later in a deciding set. They exist, but they do not headline anyone's memory.

Crowd payoff was, paradoxically, enormous — precisely because the shot was rare. Audiences had not seen forty of these on social media that week. When one landed, the surprise was total. There is a purity to a 1994 crowd losing its mind over something they did not expect, and no modern reaction quite matches that first-time astonishment.

Conversion was low. Most surviving footage shows the tweener as a desperate lob-chase that produces a weak ball, which the opponent then puts away. The shot bought a moment of beauty and usually cost the point anyway.

The Novelty Years gave us the shot's mythology. They did not give us its masterpieces.

Era two: the Golden Age

Then came the night that reset the standard. US Open, 2009, semifinal, Roger Federer against Novak Djokovic. Match point. Federer, chasing a lob into the back corner with his back to the net, hit a between-the-legs forehand that landed deep in the corner for a clean winner to set up match point — and the stadium did not so much cheer as detonate. Two years earlier, in the 2007 quarterfinals against Carlos Moyá, he had hit an almost identical shot, the first of his famous Flushing Meadows tweeners. The 2009 version is the one people screenshot.

This is the swing of the whole comparison, so we will defend it with the criteria.

Difficulty. The 2009 shot was hit at full sprint, off a deep lob, with pace, and it landed within a foot of the baseline corner. That is not a defensive flick that happens to land. That is a placed, weighted winner struck blind. On pure execution it is the highest-difficulty tweener we evaluated, and it is not especially close.

Stakes. Match point of a US Open semifinal against the man who would become his greatest rival. There is no higher-stakes tweener in the footage we reviewed. The Novelty Years cannot offer anything within a mile of this number.

Crowd payoff. Arthur Ashe Stadium is the loudest hard-court arena in the sport, and the reaction lasted the better part of a minute. Federer himself broke character and laughed. The opponent — Djokovic — could only put his hands on his hips. When the loser of the point becomes part of the celebration, the payoff is complete.

Conversion. It won the point outright. Clean winner. No follow-up needed.

The Golden Age did not invent the tweener, but it elevated it from giveaway to weapon. Nadal hit them off genuine defense and turned several into points he had no right to win. Djokovic, more rarely, used them as flat momentum-shifters. But Federer is the reason this era wins on stakes and on the single greatest example, because he had the audacity to attempt the shot at the exact moment when a miss would have been catastrophic — and he made it look like a choice rather than a gamble.

If we were ranking individual tweeners, the top of the list is mostly this era, and mostly one man.

Era three: the Showman Era

Something changed in the late 2010s. The tweener stopped being a desperation shot and became a vocabulary word. Watch a current tour event and you will see two or three between-the-legs attempts in a single match, and you will see variants the older eras never produced: the no-look tweener lob, the tweener while facing the net, the tweener as a deliberate first option rather than a last resort.

Nick Kyrgios is the patron saint of this shift. He hits tweeners he does not need to hit, off balls he could comfortably reach with a normal stroke, sometimes as a tweener-lob that drops behind a stranded opponent. The conversion rate on those is shockingly good because he is not scrambling — he is choosing. Carlos Alcaraz belongs here too, and his tweeners carry a different signature: he hits them at the net, with topspin, as drop-shot answers, with a touch that the Novelty Years could not have imagined. Daniil Medvedev and a handful of others have turned the shot into a routine part of the entertainment package.

Against the criteria:

Difficulty. This is where the era earns real respect. The modern tweener is hit with more variety — angles, touch, the no-look lob — and modern players control direction off the shot far better than anyone in the 1990s. As pure craft, the best showman-era tweeners are technically more sophisticated than the Golden Age ones, even if they rarely reach Federer's 2009 combination of pace and placement.

Stakes. Lower than the Golden Age, and this is the honest knock. Because the shot is now common, fewer of the great ones happen at the decisive moment, and a larger share happen in exhibitions, at the Laver Cup, or early in matches when a player is feeling loose. The frequency dilutes the drama.

Crowd payoff. Still huge in the moment, but smaller than the Novelty Years on a per-shot basis, for the obvious reason: audiences have seen the trick. Familiarity is the tax this era pays. A perfect tweener now earns a roar; in 1994 it earned bewilderment.

Conversion. Highest of the three eras, and it is not close. When a player chooses a tweener from a position of control rather than desperation, they make far more of them. Kyrgios in particular converts attacking tweeners at a rate the scrambling eras never approached.

The Showman Era gave us the most tweeners, the best technique, and the highest success rate. It also turned the shot from an event into a feature, and something is lost in that trade.

The comparison, side by side

Read the table and the argument falls out of it. No single era sweeps. The Novelty Years own the purity of surprise but produced no masterpiece at a moment that mattered. The Showman Era owns craft and conversion but spent the shot's scarcity to get there. The Golden Age owns the two criteria that decide the entire question — stakes and the single greatest example — and it is strong on the third.

The verdict, now that we have earned it

The best tweeners came from the Golden Age, and the reason is the one casual fans feel before they can explain it: a trick shot is only great in proportion to what it would have cost to miss. Federer hitting a blind, full-speed forehand winner on match point of a US Open semifinal is the most a between-the-legs shot has ever meant, because the moment was the largest and the miss would have been the most expensive. Difficulty and craft are real, and the modern players have more of both — but the showman tweener is hit from safety, and safety is the enemy of legend.

The Showman Era is the better era to watch if you want volume and surprise variety. The Golden Age is the better era if you want the one clip you will show a friend who does not watch tennis and watch their jaw drop. We will take the second every time.

A fair objection: we do not have a ground-truth dataset of every tweener ever hit, conversion rates included. Nobody does. Our conversion judgments come from reviewing the widely circulated footage, which over-represents the successes and the famous moments and under-represents the thousands of failed attempts that never made a highlight reel. That biases every era toward looking better than it was, and it biases the Showman Era most, because that era's misses are the least documented. We are confident in the verdict on stakes and on the single greatest shot. We are less confident in the conversion column than the table makes it look.

Who this comparison is for

This is for the fan who saw a tweener once, felt their stomach drop, and went looking for more. It is for the person who wants to understand why the Federer clip hits differently from the dozen Kyrgios clips in their feed without sitting through a coaching breakdown. It is for anyone who has argued, at a bar, about whether the old guys or the new guys did it better, and wants a way to actually settle it.

It is not for the player trying to learn the shot — we did not cover technique, footing, or when to attempt one, and you should not learn the tweener from a feature article. It is not for the analyst who wants frame-by-frame contact-point data; we did not have it and we are not going to pretend we did. And it is not for the purist who thinks the shot is a circus act that does not belong in a serious match. To that reader we say only: watch the 2009 clip again and tell us it does not belong.

Evidence grade

For the central claim — that the Golden Age produced the best tweeners, judged on difficulty, stakes, crowd payoff, and conversion — we grade the evidence Moderate. The stakes argument is essentially unarguable: the highest-pressure great tweener on record is from this era, and that is a matter of the scoreboard, not opinion. The conversion and difficulty comparisons rest on selected footage rather than complete data, and that footage flatters every era unequally. The verdict is sound on the criteria that matter most and soft on the ones we could not fully measure.

The miss costs you the match. That is why the great ones live forever.