This time, my esteemed competition has really, truly fallen flat on their faces. Philosophy of Time Travel neglected to include any actual "sports" games on his list. And Soul Kerfuffle's list is so very, very wrong that I am forced to conclude that he cannot successfully pour piss out of a boot with instructions on the heel, much less actually play a sports-related video game with anything more than a simian-level of success. So it is definitely time for the LBAM to set the record straight.
5 AND 4. NCAA Football 2004/Madden 2004 - Both of my esteemed colleagues ragged on the Madden franchise (not without reason) and by extension the NCAA Football franchise, since it is in many ways similar to Madden. Well, I think the 2004 versions of these games on the Xbox were probably the pinnacle of these particular franchises, and I link them together because the amount of fun had playing the game was increased exponentially when you could, in the NFL, draft players that you had also recruited out of high school. Nothing beat seeing NFL rosters full of actual players from colleges. The drawback, of course, was that by 2012, you had rosters full of "WR#4" and "DE#98" and "QB#2." Supposedly there was some guy who had a little internet business going where he would, for a nominal fee (I believe it was $5) mailed to him along with the memory card of your choice, return to you a completely renamed roster of all the teams in the game with real player names. Clearly, a saintly man, though I suspect an urban legend.
At any rate, Madden was still good in 2004, and featured lots of little innovations that I enjoyed; training camp drills that could help a player progress, the "owner" mode where you took over all the aspects of running a team (down to the price of beer, hot dogs, and parking) and could even relocate. I promptly made the New Orlean Saints into the Las Vegas Coyotes, complete with awesome logo and a howling sound effect when I made big plays that eventually got really, really annoying. I definitely think Madden and NCAA went downhill after this year, but they were still great then.
3. MVP Baseball 2004 - The ability to play minor-league baseball games in ridiculous uniforms in tiny stadiums with signage all over the walls. In other words, pure win.
2. Grand Theft Auto III - What, flipping wicked tricks in a stolen porsche isn't a sport? Beating hookers to death can't be a sport? Setting bums on fire with a flamethrower isn't a sport? Shooting down police helicopters, not competitive? Alright, fine. I don't have a #2 game. No soccer, basketball, boxing, or hockey game I've ever played is good enough to be on this list. Tough.
1. Earl Weaver Baseball II - Quite simply the greatest baseball game ever. EWB and EWB II paved the way for real baseball physics, full-season simulation, realistic managerial AI, 3D views, real player names, real stadium dimensions. Certainly, it was not without its glitches (like outfielders getting stuck against the wall on a hot shot to the corner - not to mention injuring themselves without fail in certain parks) but it was baseball that looked, played, and acted much more like the real thing than anything that came before it. In some cases, it looks, plays, and acts better than some games that have come long after it. Of course, one of the major bonus parts of this particular game was that it came with a book on baseball strategy by The Earl himself, and that the AI of the computer manager was essentially Earl.
I'm tempted to just say "any soccer game ever," in order to piss off SK, but that'd just be too easy.
I'm gonna go with the late 90s to early 2000s versions of All-Star Baseball, not just for the appearance of Derek Jeter on the cover, but for the fact that there was simply no f'ing way to make the computer stop messing with your lineups. Couldn't be done. Simulate more than a game or two, and you'd go check on your team and find out that suddenly your catcher had been sent to AAA, your #3 starter was now in the bullpen, and your best leadoff hitter was batting 7th. It was chaos.
Honorable Mention: Front Page Sports Football/Baseball by Sierra. Sierra, of course, rarely made bad games, and while these series eventually fell to the EA juggernaut, in the mid-90s the franchise/career options and level of statistical sophistication in these games was way, way beyond what EA offered. The Baseball series in particular featured a program called "Data In" where you could enter the stat line of any player, and he would then be in the game's database as a free agent. I loaded in the Baseball Encyclopedia's list of the top 100 players, plus a few more for good measure, and drafted teams. Good times.