True to most Wimbledon tournaments, there will be no tennis on the middle-Sunday this year. The second Monday of Wimbledon is the biggest day for tennis annually. All 32 players that are active in the men's and women's singles draws combined are slated for action on one day. That doesn't happen at the other majors and it makes the second Monday at the All England Club a special day for tennis. One tantalizing match that is slated to take place features #Roger Federer and #Grigor Dimitrov. This is the match that Dimitrov should challenge Roger Federer in.

However, when I write this, I feel that an explanation of what I mean is needed.

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My use of the word "should" is not meant to be taken as a prediction. For instance, if a scientist told you that an asteroid "should" hit the moon then his statement would be taken as a prediction.

My use of the word "should" is more prescriptive as in "You should get your driver's license when you are an adult." In this way, Dimitrov should challenge Federer at Wimbledon 2017: It's that time in the Bulgarian's career when he really should start keeping the 30+-year-olds out of the big matches. With Federer due to turn 36 in about a month here, it's time for a 26-year old Dimitrov to get his Roger-Federer-beating license.

Dimitrov has loads to prove on tour

Dimitrov used to be the heir apparent to the World No. 1 ranking. If I had to answer "yes" or "no" to the question, I would still maintain that at some point in the five years ahead he will hold the No.

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1 ranking for at least one week. However, Dimitrov is 0-5 against Federer heads-up still. That record includes a total of three losses in the last two seasons, one of which came in a Grand Slam.

Dimitrov part of the Lost Generation

Dimitrov is part of the #lost generation of Men's Tennis, the guys that simply have not been able to supplant the Big Four despite significant advantages in age difference. Milos Raonic, Kei Nishikori, David Goffin, and Dimitrov are the core four in the Lost Generation. These guys don't have a Grand Slam title between them - nor do they own a Masters Series shield. The Big Four (plus Stan Wawrinka) have handed them losses at so many big stages.

That "should" turn around at some point, but if it happens at Wimbledon 2017, then it won't be Goffin or Nishikori that do it. Goffin is out pre-tournament with injury while Nishikori went out via the upset. Dimitrov or Raonic could win Wimbledon still, but it looks like they'll need to beat the big dogs in the week ahead.

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Federer, Rafael Nadal, Novak Djokovic, and Andy Murray all remain alive in the round of sixteen. Those are the headliners for the men's draw on Monday. Meanwhile, Raonic is being relegated to Court No. 2 for what looks like a coin toss against Alexander Zverev. If Raonic and Dimitrov both won then maybe the Lost Generation might find a Wimbledon title this season.

But wouldn't it be funny if the Lost Generation stayed lost permanently? What if Raonic, Dimitrov, Nishikori, and Goffin never won a major? What if the Big Four kept beating them until Alexander Zverev and Dominic Thiem start winning majors?

Dimitrov is 26 and he should beat Federer on Monday in the same way that one should, with people wagging fingers at you if you don't, get your high-school diploma by a certain age. But, to be clear, that doesn't mean I'm predicting that Dimitrov will win as guys around his age just don't know how to play tennis like the older guys do. Wimbledon 2017 could still be the long-awaited changing of the guard in men's tennis, but that doesn't mean that such an event is actually to be expected.