1988 - doesn't really matter. It was a tv special and had no real bearing on storylines; indeed, it's only fairly recently that WWE have really started to acknowledge it
1989 - Million Dollar Man, after he had such an important year in 1988. I never really got why Big John Studd won it, almost like a thank you present for years of service
1990 - Having read the views on here, Mr Perfect would have made a good winner. And he did have a Saturday Night's Main Event match with Hogan (two in fact, one count out win)
1991 - Hogan was always pencilled in as #1 contender, first for a Warrior rematch and then when Slaughter took the belt. Even though the title shot wasn't on the line officially in the Royal Rumble, it makes perfect sense for Hogan to win here and use it to become the number one contender for Wrestlemania VII
1992 - Flair keeps the win, but should have faced Hogan at Wrestlemania
1993 - Randy Savage. I'd have Earthquake and Yokozuna somehow eliminate each other, building a match between those behemoths at Wrestlemania IX, with Savage winning the Rumble; maybe last eliminating IRS who was easily one of the most over heels in the business at the time (rewatch old Raws on the Network and you'll see what I mean) - then Savage faces Bret Hart at Wrestlemania, losing. Bret loses to Yokozuna (who defeats Earthquake at WM, thus legitimising his threat further) at King of the Ring (Narcissist Lex Luger wins the tournament, the fans start appreciating him more, and the rest of 1993 happens exactly as it did.)
1994 - stays the same, a really well booked Rumble match with its best finish IMO
1995 - the same, though more time between entrants, less quick eliminations, better booking and Shawn v Diesel is the actual main event of Wrestlemania, not playing second fiddle to Lawrence Taylor
1996 - British Bulldog - i'd have loved to see Bret v Davey clash one more time in the main event of Wrestlemania. Given their history, with two brilliant and very close matches, tied 1-1, the Iron Man stipulation would have made far more sense than just throwing Shawn and Bret into it
1997 - Shawn Michaels - make Shawn a repeat winner, but not in consecutive years. Have him win the Rumble at the Alamodome in his home town, with Bret Hart going into Wrestlemania as champion
1998 - same - no one was hotter than Stone Cold in January 1998
1999 - honestly not sure about this one, tempted to keep it the same, but McMahon is forced/cajoled into putting his title shot on the line at St Valentine's Day Massacre
2000 - same
2001 - same given we got Wrestlemania 17 out of it, the best card ever IMO
2002 - Kurt Angle. There was no need for Triple H to win the Rumble, unless Austin was champion heading into Mania. That is the ONLY reason Triple H should have won. Also it started off the sporadic trend of returning headliners winning the Rumble. Angle should have won, and faced Jericho at Mania in what could have been a technical classic
2003 - same
2004 - same
2005 - would have finished on a double elimination, 1994-style. Both Cena and Batista challenged for their respective titles at Mania anyway
2006 - this is where I'd probably have put Triple H's win, especially as he fought Cena at Wrestlemania anyway; I was never sold on the Rey Mysterio experiment
2007 - same, with one of the best 'last two' sequences in Rumble history, only bettered by 1995 and the actual finish from 1994
2008 - same
2009 - same - about time a faction led their leader to a Rumble win
2010 - probably John Cena to be honest. I don't think Edge should have won it, he didn't need a Rumble win to have a reason to feud with Chris Jericho, his former tag team partner
2011 - CM Punk, with assistance from the new Nexus; but I'd have had Randy Orton keep the belt, so Punk v Orton still happens at Mania, just for the title. The Miz cash in can still happen, but later on
2012 - Chris Jericho, for all the reasons mentioned on this thread
2013 - the Rock - instead of announcing on Raw 1000 that he's challenging for the title, Rocky announces he's entering the Royal Rumble match. He wins, and goes on to beat CM Punk for the title at Wrestlemana
2014 - Daniel Bryan - for all the calls for Bryan to win a year later, he SHOULD have won in 2014. Personally, I still think the plan was for Bryan to win the title at Mania all along, and they completely played us, but I would have loved to have seen a Bryan Rumble win
2015 - I would actually keep this the same, but book the match FAR FAR better. One of the worst booked matches in WWE history. Screw Big Show and Kane eliminating everyone the fans cared about (Ziggler, Ambrose, Wyatt...), Reigns could have eliminated them. And Daniel Bryan should 100% NOT been in it. The only reason he should have been in it would be if he was booked to win it, ridiculous otherwise
2016 - Dean Ambrose. Have Ambrose win the title that his friend wore into the Rumble, with Triple H not in the match but somehow screwing Reigns, against the knowledge of Ambrose. Cause dissection amongst the friends and have Reigns beat Ambrose for the title at Wrestlemania, possibly involving an Ambrose heel turn, in a no holds barred main event. Really bring out the lunatic in Ambrose