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How do you know when you’re a truly sick fan of a sport? One measure is how much you like watching your particular game of choice when it’s at its most meaningless. I certainly qualified as a kid. I can’t think of many times when I've enjoyed tennis more than during the desultory fall European swings of the 1980s and 1990s. My dad and I loved seeing the muted, yawning crowds; hearing the stultifying thud of the ball hitting the racquet in a cavernous arena; laughing at the obscene winners’ checks and over-designed trophies—once derided as “golden helicopters” by Martin Amis—and getting to watch guys like Brad Gilbert and Michael Stich (Marat Safin, Nikolay Davydenko, and David Nalbandian are their descendants), who almost never won Slams, show off their best stuff when there was little more than money on the line. It was must-see viewing for any tennis junkie with a sense of humor.

I mourned when the granddaddy of all joyless and hollow tennis events, the ITF’s Grand Slam Cup, was discontinued. Somewhere along the line it merged with the ATP’s World Championship to become the more dignified but maybe not as enjoyable Masters Cup. That’s been true of the fall season in general in recent years. It still seems tacked on; it’s still a time for the second tier to shine; and the crowds still look a little bored. But the mandatory Masters events in Madrid and Paris have drawn better fields and made the events seem like more than just excuses for sponsors to display their logos. On the men’s side, Roger Federer and Rafael Nadal have each won in Madrid, and this year the No. 1 ranking is still undecided on either tour.

Despite this respectability, I still like the fall season. Part of me thinks we could live without it, but when the Tennis Channel shows every round of Madrid and Paris, and the best eight women and best eight men spend a week fighting it out at the season-ending championships, I know I can’t complain. Like any other season, fall ball deserves its preview. Here are five things I’ll be looking for:

1. Who will be the year-end No. 1s?

Nadal is the likely candidate on the men’s side. He’s ahead of Federer by 1100 points in the official rankings (for perspective, a Masters event is worth 500 points and most other tournaments about half that), and Federer is ahead of Novak Djokovic by another 1100. Nadal needs to defend a quarterfinal finish in Madrid, a runner-up finish in Paris, and a semifinal run in Shanghai. Federer is playing two additional smaller events, Stockholm (worth 225; he didn’t play it last year) and Basel (worth 250; he won it last year). The race isn’t tight, but it isn’t over (as far as I know; I'm not an expert), which puts something on the line when these guys play.

The women’s race is much tighter, of course. Serena Williams is No. 1 now, but Jelena Jankovic is just behind her and Dinara Safina and Ana Ivanovic are within striking distance. The wild card is Serena. How much will she play? Being No. 1 has never been a goal in itself for her. We know Jankovic will crank out points, Safina won a Tier I in Tokyo last week, and Ivanovic will likely get better the more she plays. It would be nice to see it come down to the big, $4-million-dollar, season-ender in Doha. I can just see the winner flying off in a golden helicopter.

2. Can anyone become the David Nalbandian of 2009?

It’s easy to imagine Nadal, Federer, and Djokovic suffering from a slight, maybe even subconscious lack of motivation at this point in the season. Last year it was enough to give Nalbandian a chance to hoist the trophies in Madrid and Paris. If the same thing happens this time, you’d have to think Juan Martin Del Potro would be voted most likely to succeed. He’s won four smaller events, reached a Slam quarter, and cut his teeth in Davis Cup. Next on the agenda is a Masters title. But blocking his path may be Andy Murray. He’s had a long year, just like the Big 3, but he’s gathered momentum in the last four months and has just one Masters win to his credit, so he should be hungry for these. He also shouldn’t be any more doubts about whether he belongs with the big boys.

Sleeper: Marin Cilic—tall helps indoors.

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3. What will the atmosphere be like at the Sony Ericsson Championships in Doha?

Like I said above, this early November, megabucks event far from the sport’s capitals feels like Grand-Slam-Cup, golden-helicopter time. The WTA’s season-ending round robin was dead on arrival in L.A. earlier this decade and was quickly yanked out of Madrid in favor of the money in Doha. You can’t blame the tour for making the best deal it can make, but will the upshot be an airless, buzzless finale? The ATP’s shift in the opposite direction—its season-ending event travels from Shanghai to London next year—feels like the smarter long-term move in terms of visibility and fan interest. But we’ll see: The men’s tournament in Dubai this past year didn’t appear to be jammed, but it was livelier than I thought it would be. Maybe Doha will be the same for the women. Whatever the fans were like in Madrid, and they were hardly a raucous bunch, the tournament gave us the women’s match of the year last year, a three-set final between Justine Henin and Maria Sharapova. Unfortunately, neither will be in the area this time.

4. How much will Novak Djokovic put into his fall campaign?

I’m curious about this not just because he ran out of gas last year, but because he’s shown a tendency toward ambivalence about his fortunes as 2008 has progressed. Sometimes he competes with all he’s got, other times he looks like he’s trying to lose without actually tanking. (That's not an easy balance to strike; he might as well just try his hardest.) Now that he’s not progressing up the rankings anymore, what will his commitment be from match to match and week to week when there’s nothing huge on the line for him?

5. Who is going to win the Davis Cup?

The good news is that it’s Spain vs. Argentina; the bad news is that the Argentines are trying to play it on carpet indoors. If that happens, some of the traditional emotion of DC in Buenos Aires may be muffled, and the glory of seeing these two clay-court nations face off on their native surface would be missed.

Still, it’s a smart move. Why give Nadal a chance to beat you twice on dirt? Even indoors, I like his chances against Nalbandian or Del Potro, though both matches would be wars. Ferrer strikes me as the chink in the singles armor for Spain, and while that team is more settled with its doubles pairing of Lopez and Verdasco, Nalbandian is more talented than either and can carry his partner on a good day. Argentina has never lost at home. But as of now, and barring an injury to Nadal, I’ll pick Spain to close out the 2008 season on top. And to walk away with a very nice, very traditional trophy.