So, I got into a strange thought about how we haven't had an NHL game on a dedicated handheld since NHL '07 on the PSP. Basically, I still play NHL '07 since it is the best handheld game of NHL that we have and it is almost a decade old. This is similar to how people still play and adore NHL '94 or ESPN NFL 2K5 because in many cases the experiences haven't been improved upon or replicated.
I thought this could be an interesting topic since we often think that old sports game immediately become irrelevant. For the most part, that statement does have some truth (the countless versions of Madden). However, there are some sports titles that are still fun and interesting despite being outdated by technology, rosters, and teams. For this list, we should avoid stuff like Mario Golf etc. since those games really don't have anything that date them outside of technology.
What are your 10 most interesting/relevant sports games to play today?
My tentative 10 in no particular order:
1. NHL '07 - PSP
As I mentioned before, there hasn't been an NHL game released on a dedicated handheld console since this entry. It also happens to be a very competent game of hockey with decent commentary, gameplay, and graphics. (Note: I am aware of Backyard Hockey for DS which may have come out around the same time.)
2. ESPN NFL 2K5 - Xbox
Aside from the fact that this game is interesting from a historical standpoint. NFL 2K5 was just an incredible game of football that even fans that didn't enjoy the game could get into. The presentation was incredible for its time and still is incredible to this day. The game released at $19.99 against a full priced Madden. It's just too bad that EA snatched up the NFL license after this and we were never given the opportunity to see the series grow further. NFL 2K5 is still considered the gold standard for a NFL simulation to this day.
3. MVP '07: NCAA Baseball - PS2
A very similar situation to the one above just reversed. At the time, EA was really doing a great job with it's MVP Baseball series. However, 2K snatched up the MLB license as "payback" to EA and left EA without any license for their baseball game. Therefore, MVP College Baseball was created and gave sports fans something they never had before, college baseball! This game is just fantastic and still great to play to this day. It's great to take my Terps and play through this. The series only had two entries for '06 and '07. I doubt we will see another game like this for quite some time.
4. Arena Football: Road to Glory - PS2
Another "one-off" series that will probably never see a new entry. RtG was the second and last game based on Arena Football. Yes, there was a game based on Arena Football.

EA basically was trying to grab as many exclusive licenses as possible. The game isn't bad (quite fun) and is a nice diversion for those bored of Madden.
5. High Heat Baseball 2004 - PS2/Xbox
The High Heat series (famous for it's commercials featuring Sammy Sosa "It's so real") was about the only decent thing the house of 3DO was putting out right before their bankruptcy. The license was acquired and is still owned by Microsoft who has done absolutely nothing with it. HH Baseball was a fantastic game at the time and still has a pretty strong following more than a decade later.
6. Wayne Gretzky's 3D Hockey - N64
Wayne Gretzy's 3D hockey did for hockey what NBA Jam did for basketball. It's basically over the top 3 on 3 hockey action. I'll be blunt, I love this game. It's an incredible blast with a group of people as well. I don't think this game will ever get old for me. It's accessible, fun, and competitive. It's the perfect multiplayer game despite it being nearly two decades old!
7. NHL Hitz 20-03 - Xbox
Might as well mention this one while we were discussing Wayne Gretzy's 3D Hockey. Hitz is very much the spiritual successor to the aforementioned game. However, Hitz is also a surprisingly deep hockey game that has aged really well. It's a blast to play and unfortunately it died off with Midway.
8. NBA Street Series (still deciding which entry I enjoyed the most)
A really great series that unfortunately faded away for whatever reason. NBA Street is "pick-up" style basketball and uses famous parks and street courts as the venues. It has similarities to NBA Jam, however, NBA Street is a much stronger single player experience.
9. NHL 2002 - Xbox
I admit it, I love hockey and I love hockey video games. I think that EA crafted an almost perfect game of hockey with NHL 2002. In fact, most of the NHL games from EA around the time were just great. I included this one as well to show that EA really has let the NHL series slide off into a perpetual state of mediocrity. There is something wrong when previous versions of NHL got it "right" especially so long ago. NHL '15 is nothing short of a disaster and '14 wasn't any better. *As a bonus, the commentary was brilliant and comedic in NHL 2002. To be honest, I don't think EA would allow some of the stuff they said in a new game.
10. College Hoops '08 - XBox 360
I'd say this is the last good college basketball video game. I know that EA released two games past this one ('09 and '10). However, they were never as good as the last one put out by 2K Sports. Unfortunately, 2K didn't pursue to renew the NCAA license and basically abandoned the series. I'm not sure if it was strictly because it wasn't worth it for them financially. Regardless, EA acquired the license but ended the series in 2010. We have not seen a new college basketball game since and we might not ever because of the NCAA and their craziness.
There are plenty others that I find interesting for various reasons:
Blast Lacrosse (the one and ONLY Lacrosse game on any video game console)
NHL Rock the Rink (EA's take on Midway's NHL games)
NHL '94
NBA Jam
NFL Blitz
Blitz: The League
All Pro Football 2K8 (2K's last grasp at a football game without the NFL license)
Mutant League Football
NHL 2002 (Gameboy Advance Version)
NHL Slapshot
NHL 2K11 (Wii)
MVP Baseball 2005
Microsoft XSN - NFL Fever, NBA Inside Drive, NHL Rivals
NBA Courtside 2002
Ken Griffey Jr. Baseball
World Series Baseball '98 (Saturn)
MLB Power Pros 2008 (Wii/PS2)
Tecmo Super Bowl
If this has been done before, just ignore it and I will accept my searching skills to be deficient.

I know there will be some users (RSG) here that will be interested in this.