Garber: There's a lot to like about both these matchups, but I'll be keying in on the Federer-Raonic match. This is a classic spring/autumn encounter, the kind that Federer used to dominate. One of the storylines coming in was whether the 17-time Grand Slam champion might add to that total here. The consensus was that this might be his last decent chance. Some things had to happen for him, and they have. Now he won't have to beat Nadal or Murray on his way to the title. Raonic -- and a depleted Djokovic -- just might do the trick.
Bialik: Federer relishes these matchups with younger generations, partly because he usually wins them but also because of his appreciation for the sport's history. He speaks often with fondness about his 2001 win here over Pete Sampras, the only time they played an official match as opponents. Federer would sound egotistical when he says he'd like to give younger players the chance for a similar match, if it weren't true that they also want the chance to play him while he's still near his best. So tennis historians should hope for a Federer-Dimitrov final. Raonic and Djokovic won't agree, but they and Dimitrov should have many more chances to play one another in Slam semis and finals. Can Dimitrov get to the final? I think he will if he plays as intelligently and ably as he did against Murray.
Wilansky: Dimitrov, like Federer, came into Wimbledon fresh off a grass-court tuneup win. He's riding a nine-match winning streak, and on Monday he will move into the top 10 in the official rankings. More than anything, though, we've seen the maturation of a Bulgarian star once known for wearing his party hat into the wee hours of the morning. Times have changed. The other day, he was sitting by himself in a local restaurant with only a smoothie and smartphone in hand. No entourage, no distractions. A year ago, the biggest headline Dimitrov made came via Serena Williams when she said he was a man with a "black heart." But he has really settled down, and if I had to pick one of these 23-year-olds to pull off an upset, it would be Dimitrov -- especially because Djokovic's form was a bit spotty in his last match against Cilic.
Garber: That's interesting because you picked Djokovic to win here, Mr. Tennis Editor. You also picked him to win the French Open -- as did I -- and how did that work out? These days, he's in an interesting place. When I saw him thump Nadal in the final at Miami, I thought he might give him a go at Roland Garros. When he drilled Nadal in the last two sets in Rome, I knew he was going to win in Paris. And then, although he said winning the French was his priority for the 2014 season, Djokovic came up woefully short in the final. Now he's slipping and sliding all over the place, like a cow on ice. Not quite sure what to make of his match with Dimitrov. I will yield to our numbers cruncher ...