Since I did end up deciding to include an extra four teams to make it a perfect 16-team bracket, placements were done by “seeding” the teams in chronological order, and then slotting the four leftover teams in spots where they wouldn’t be playing against their own year. I’ll say who I think would win the matchup, and then if Pat disagrees with any of my choices, we’ll either discuss it further, or in that case go to a simulation site. 

1997 Southeast (PG Mike Bibby, SG Jason Terry, SG/SF Cuttino Mobley, F Paul Pierce, C Brad Miller, Anthony Johnson, Brian Cardinal, Raef LaFrentz)
vs.
2002 Midwest (PG T.J. Ford, SG Kyle Korver, SF Josh Childress, PF Udonis Haslem, PF/C Drew Gooden, Royal Ivey, Darius Songaila, Matt Bonner)

’97 Southeast is basically getting a bye, as I don’t see any way the 2002 team can hang with the impressive starting lineup their opponents are trotting out.

2004 Atlanta (PG Deron Williams, G Chris Duhon, SF Luol Deng, F Andre Igoudala, PF Jason Maxiell, Luther Head, Francisco Garcia, Channing Frye)
vs.
2005 Syracuse (PG Raymond Felton, SG Randy Foye, SF Danny Granger, PF Charlie Villanueva, PF/C David Lee, Kyle Lowry, Rashad McCants, Sean May)

A very tight matchup with two solid teams, but I think Granger’s squad has a slight edge because of their better bench and better inside presence offensively. 

2001 Midwest (PG Kirk Hinrich, SG Gilbert Arenas, SF Josh Howard, SF/PF Richard Jefferson, PF David West, Troy Murphy, Luke Walton, Brian Cook)
vs.
2008 Midwest (PG Mario Chalmers, SG O.J. Mayo, SF Michael Beasley, PF Darrell Arthur, C Roy Hibbert, Brandon Rush, Bill Walker, Darnell Jackson)

The 2008 squad could become a very solid team in a few years, but right now they have no chance against a very good 2001 stating lineup.

2000 East (PG Speedy Claxton, SG Mike Miller, SF Shane Battier, PF Carlos Boozer, C Sam Dalembert, Quentin Richardson, Desmond Mason, Mike Dunleavy)
vs.
2007 South (PG Ramon Sessions, G Mike Conley, SF Daequan Cook, C Brook Lopez, C Greg Oden, Acie Law IV, Javale McGee, Robin Lopez)

Two teams with some of the better inside talent in this tournament, but 2000 dominates this game with superior talent at most positions.

1999 South (PG Baron Davis, G Steve Francis, G/F Michael Redd, PF Ron Artest, C Etan Thomas, Earl Watson, Matt Barnes, Juan Dixon)
vs.
2005 Albuquerque (PG Chris Paul, G Jarrett Jack, G Nate Robinson, G Jordan Farmar, PF/C Ronny Turiaf, Aaron Afflalo, Adam Morrison, Pops Mensah-Bonshu)

Even though 2005 has the best player on the floor, the rest of the team is not even close to a match for the loaded front four in 1999. 

2002 East (PG Steve Blake, SG Ben Gordon, SF Caron Butler, F Tayshaun Prince, C Emeka Okafor, Travis Diener, Jarvis Hayes, Chris Wilcox)
vs.
2007 Midwest (PG Aaron Brooks, F Thaddeus Young, F Anthony Morrow, PF Carl Landry, PF/C Al Horford, Joakim Noah, Marreese Speights, Corey Brewer) 

2007 definitely has some talented players, but they’re so front-court loaded that there’s no way they could keep up with the 2002 East team. 

2003 Midwest (PG Devin Harris, G Mo Williams, G Dwyane Wade, F Chuck Hayes, F Kelenna Azuibuike, Luke Ridnour, Keith Bogans, Steve Novak)
vs.
2006 Washington DC (PG Rajon Rondo, SG Brandon Roy, SF Rudy Gay, PF Josh Boone, C Hilton Armstrong, Dee Brown, Shannon Brown, Paul Davis)

The biggest matchup of the first round and it’s a shame that one of these teams has to go. Rondo Roy and Gay is one of the best threesomes in the tournament, but in the end I think their lack of depth hurts them, as does the fact that they’re playing against the best player to come out of college since Tim Duncan. The Midwest takes it in one of the games of the tournament. 

1998 East (PG Earl Boykins, SG Vince Carter, SF Richard Hamilton, PF Antawn Jamison, C Brendan  Haywood, James Posey, Morris Peterson, Eduardo Najera)
vs.
1997 West (PG Andre Miller, G Brevin Knight, SF Keith Van Horn, PF Tim Duncan, C Jamaal Magloire, Ron Mercer, Michael Olowakandi, Nazr Mohammed)

An in-his-prime Andre Miller and Tim Duncan would work great together, especially if they had a good wide-open shooter like Van Horn to dish to when appropriate. Unfortunately, they’re going up against an even more impressive squad. Boykins might start at the point, but I’d guess that Hamilton would take over the duties for much of the  game, allowing James Posey to play major minutes. 1998 East wins this game in another close one, as there’s only so much Duncan and Miller can do alone.