Bold = Probably a discussion to be had.
-------------- Start: 03 Wimbledon ----------------
05 AO: Federer beats Safin, likely beats Hewitt in the final. +1.
06 AO: Nalbandian makes the final over Baghdatis, but I don't think that's enough to pull away the title.
06 Wimbledon: Federer wins even more convincingly, as Nadal loses R2.
07 Wimbledon: Djokovic does not get into a lengthy QF 5-setter, beats Youzhny/Berdych in the SF, but still loses to Federer.
07 USO: Federer beats Ferrer in the final, as Djokovic loses to Stepanek.
08 AO: Tipsarevic upsets Federer, not Djokovic. Still, outcome doesn't change.
08 Wimbledon: No change, but Nadal wins in straights instead of 5 sets.
08 USO: Murray doesn't make the final. Nadal or Del Potro do, but still lose to Federer.
-------------- End of 08: Federer +1, Djokovic +0, Nadal +0 ---------------------
09 AO: Federer loses to Berdych in the R4, Roddick meets Nadal in the final and loses.
09 RG: Federer loses to Haas, who loses to Delpo. Delpo wins RG. -1 Federer.
09 USO: Federer beats Delpo in the final. +1 Federer.
09 swaps slams for Federer and Delpo, huh...
10 AO: Djokovic-Federer SF occurs. Federer likely wins and goes on to beat Murray in the final.
10 RG: Djokovic does not lose to Melzer, instead to Nadal in the SF. Nadal instead slaughters Berdych in the final.
10 WIM: Federer loses R1 to Alejandro Falla, Berdych to Istomin in R3, Djokovic to Rochus in R1, Nadal to Haase in R2 (or Petzschner in R3).
Melzer-Istomin QF + Hewitt-Lu QF. Hewitt becomes a finalist. Murray-Soderling is likely the true final here, and I'd lean Murray. Murray +1, Nadal -1.
10 USO: Federer loses the final to Nadal instead of Djokovic.
11 RG: Nadal loses R1 to Isner. Murray to Troicki in R4. Soderling is a finalist. Federer picks up his Career Grand Slam here. Nadal -1.
11 WIM: Federer makes the SF against Djokovic, probably still loses. Everything else remains the same.
11 USO: Unless Isner beats Nadal in the SF, Federer ends up beating Nadal in the SF, I think. Federer +1, Djokovic -1.
-------------- End of 11: Federer +3, Djokovic -1, Nadal -2, Murray +1 ---------------------
12 AO: Murray takes out Djokovic in the SF, then Nadal in the F. Djokovic -1, Murray +1.
12 RG: Seppi takes out Djokovic in R4, Delpo or Tsonga end up the finalist here. Still lose to Nadal.
12 WIM: Benneteau takes out Federer R3, Djokovic makes the final. Tough to pick here, but I'll go with Djokovic over Murray.
13 AO: Surprisingly despite a ton of 5 setters, no real impact.
13 WIM: Verdasco upsets Murray in the QF, Janowicz or Verdasco is the finalist, Djokovic wins. Djokovic +1, Murray -1.
13 USO: Wawrinka d. Djokovic, still loses to Nadal.
14 WIM: Cilic upsets Djokovic in the QF, Dimitrov loses to Dolgopolov in the R3, leaving Murray-Cilic as the SF. Let's say Cilic wins, but I have trouble seeing Cilic beat 2014 Federer. Federer +1, Djokovic -1.
14 USO: Raonic beats Nishikori in the R4, leading to Raonic/Wawrinka in the SF against Djokovic. Let's still say Djokovic loses as I don't want to cause trouble here. Cilic beats Monfils in the SF, winning the final against whoever it is.
15 RG: Some trouble here. Tsonga beats Nishikori much more easily, then maybe he does better against Wawrinka, either winning or wearing him out? Djokovic also beats Murray convincingly in the SF, making him much fresher for the final. Could change something. Let's say it doesn't.
15 WIM: Anderson upsets Djokovic in R4, Wawrinka vs Cilic SF, I think Cilic wins. However, Federer wins the final. Federer +1, Djokovic -1.
15 USO: Nadal not upset by Fognini in R3, but I still doubt he beats Novak in the QF. No change.
-------------- End of 15: Federer +4, Djokovic -2, Nadal -2, Murray +1 ---------------------
2016 AO: Nadal not upset by Verdasco in R1. Still don't think it changes much. Djokovic d. Raonic in the final.
16 WIM: Querrey out R1 by Rosol, unable to serve and destroy Djokovic. Djokovic survives until the QF, where Goffin awaits. I also don't think Goffin beats Djokovic. Cilic beats Federer in the QF, and I think Cilic is the one to finally take out Djokovic. Murray beats Cilic.
16 USO: Wawrinka loses to Dan Evans in R3. Pouille loses R2 before taking out Nadal. Nadal likely still goes out (say to Monfils or Djokovic). Delpo-Murray SF. It doesn't really matter who wins because I can't decide who of Djokovic/Delpo/Murray gets the win. Going by sets won against Real Stan, it's tied up. So via games, Delpo got 17, Nishikori (Murray standin) got 17, so Murray probably a bit less, and Djokovic got 19. Going with Djoko. Djokovic +1, Wawrinka -1.
17 AO: Nadal does not survive Zverev in the R3. Djokovic, however, does survive Istomin in R2. Could go many ways, but let's say Dimitrov takes out Djokovic, Federer beats Dimitrov in the final.
17 RG: Nadal murders Murray in the final instead of Stan. Djokovic loses even earlier.
17 WIM: Murray survives the QF, maybe beats Cilic, but is unlikely to beat Federer.
18 AO: Nadal survives the Cilic QF, faces Dimitrov in the SF (wins), and goes on to lose to Federer in the final (Federer d. Cilic d. Nadal).
18 WIM: Federer doesn't lose to Anderson in the QF, maybe to Isner in the SF but probably not. Delpo beats Nadal in the QF, then loses to Djokovic in the SF. Djokovic beats Federer in the final.
19 USO: Federer d. Dimitrov in the QF, loses to Medvedev in the SF.
-------------- End of 19: Federer +4, Djokovic -1, Nadal -2, Murray +1, Wawrinka -1 (no changes, wild) ---------------------
20 AO: Thiem loses to Bolt (if Bolt doesn't lose to ARV), but this is a strange case. ARV could just as easily win those 2 sets. Nadal moves on to the SF, Sandgren b. Federer but not Djokovic. Tough to say if Thiem should win the whole thing or Nadal/Djokovic. As it stands, I'll say it remains as is.
20 USO: Busta doesn't win R1, Uchiyama does. Djokovic doesn't get angry at Isner, no default. Likely wins the tournament. If not, then I don't know who since PCB would beat Zverev but Zverev would beat Thiem, so does PCB win? Djokovic +1?
21 AO: Nadal makes the SF, loses to Medvedev.
21 RG: Cecchinato d. Musetti R3, keeping Djokovic from losing R4, (but still maybe does). If he does, though, Tsitsipas still wins the final. Djokovic -1.
21 WIM: Cilic/Medvedev d. Hurkacz, maybe, but I still think Federer loses the tournament.
22 WIM: Sinner d. Djokovic in the QF, Fritz d. Nadal, Goffin d. Norrie. I guess Kyrgios wins? Djokovic -1.
22 USO: No real change but Sinner beats Alcaraz, so I guess maybe Sinner wins?
-------------- End of 2023 AO: Federer +4, Djokovic -2, Nadal -2, Murray +1, Wawrinka -1 ---------------------