FIFA SOCCER ON LEGENDARY! The only time where Barcelona FC can lose to a half a star club from the n-power league 2.
Super Soccer on the SNES has a tournament mode in which the player is put up against all of the other teams in the game, one by one until the player has defeated them all. So what happens when all of the teams are defeated? The player wins and the game is over, right? Wrong. The player is put up against one final team that doesn't even exist on the select screen. A team that is so hard, it makes the rest of the game look like a joke in comparison. A team that clearly only exists because some sick game designer wanted to laugh at your sad attempt at beating it. To actually win against this team is next to impossible. What team is this? Why of course, it's team NINTENDO!
Mike Tyson's Punch Out!! is notorious for its difficulty. The final three or four boxers on the World Circuit are absolute monsters, to say nothing of Mike himself. It gets really upsetting to work your way through the World, finally beating Super Macho Man for the title and earning your shot at Mike Tyson...only for him to knock you down in one hit.
It's similar to Castlevania 2, actually, where most of the challenge is simply finding out what you need to do (King Hippo is the perfect example).
The remake for the Wii isn't too bad...until you beat everyone and win the World Title, which unlocks the absolutely merciless Title Defense Mode. You have to fight every boxer you've beaten before, except they've all learned new tricks that are guaranteed to cause headaches for players. To put this in perspective, Title Defense Glass Joe, the very first boxer in the game sporting a 1-100 career record, is almost as hard as Mr. Sandman, the undefeated champion who you just beat. And he's the first, and undoubtedly the weakest, guy you'll fight in Title Defense.
It gets better. After you win that, you can play against the defenders in random order, only this time, 3 losses and you're retired. No, not "let's try that again" retired, more like "the career mode on your save file is locked forever and you'll have to make a new file and start all the way from the beginning" retired. Oh, and you no longer have the options to restart or duck out of a fight if it goes badly - no Save Scumming for you this time. Your "reward" for winning 10 fights of that? A new option in exhibition mode to make every attack from every opponent a one-hit KO, and to remove their tells (ie they don't flash red before attacking anymore).
But wait, there's evenmore! We almost forgot the additional challenges that come in Exhibition mode, which must be completed to unlock that boxer's music and audio clips. Half of them are fairly simple to accomplish (Find all the ways to get stars, win the fight in so many punches.) if you can figure out the tricks behind them. The others crank up the sadism to 11. TKO Soda Popinski with 1:11 left in Round 1? Beat Mr. Sandman without ever dodging or blocking? Defeat Title Defense Piston Hondo without ever losing a heart? Good thing you get unlimited attempts, because you will need them.
And the worst thing of all is Mike Tyson's replacement if you get far enough in Title Defense... DonkeyKong. The mere fight, that is. His Exhibition Challenges are likely to drive players insane until they can figure out the right strategy to beat them.
Super Punch Out! for the SNES is arguably just as hard as its NES predecessor. For one thing, unlike Tyson, each match is only one round long, and you can't win by decision. So if that three minute timer runs out, you automatically lose, no matter how well you performed and how many points you racked up. And it's not like your opponents are any less beastly than they were before; Bald Bull is back in this game, and he's one of the easier fights.
Tecmo Super Bowl for the NES quickly became an exercise in futility. On defense you were essentially guessing what play the offense was running. If you guessed right, your players moved ridiculously fast and you would, theoretically, stuff the play. Great, until the playoffs, particularly the Super Bowl. To increase difficulty, they just gave the CPU players superhuman abilities. Calling THE CORRECT PLAY on defense and still having Bo Jackson run directly through your entire team for a 90 yard touchdown run was a common occurrence, and the Super Bowl version of Jerry Rice would catch passes, in quadruple coverage, approximately 110% of the time.
Ninjas shouldn't be allowed to play basketball. It's not fair. They're ninjas.
Tecmo's Captain Tsubasa games can be very hard if you don't play very well. Even by the time you get to control Japan, you'll be force to play with extraordinary powerful national teams with super shots and saves.
Captain Tsubasa Vol.2: Super Striker has Tsubasa and his weak team at one time goes against the 97% complete Japan full of special shots and saves. Very latter teams are easily put into That One Boss, for instance, Germany with Schneider who gets stronger every time you lead the score upon him, and Brazil with a goalie who simply block every things but Game Breaker skills, and 2 strikers who will blow the net and Wakabayashi's hands out of misery. It's quite impossible to win without doing Level Grinding by losing these matchs over and over again.
WWF No Mercy is pretty easy for the most part, as you can win most fights by starting with light moves and moving on to flashier stuff when your Attitude turns orange. But on Championship mode, there are various storylines where Vince McMahon gives you an offer to make you part of the Corporation. If you refuse, you get a gauntlet of three or more No Tag Handicap matches aginst Vince's strongest flunkies in a row.
Neverputt has Tricky Golf course. To score each hole on par, pixel-perfect and sometimes well-timed hits have to be made.
Winnie the Pooh's Home Run Derby will rip your soul from your body and send it to rot in the Hundred Acre Wood. Christopher Robin will become your God.
Compared to other games in the series, Tony Hawk's Pro Skater 2 is this. Certain levels practically require you to get crazy air to get anywhere, and you can't keep a combo going for that long unless you use a lot of manuals. These aspects of the game caused some players to consider other games in the series too easy. In actual fact, it was just that the level design in 2 was much more challenging than even the first game.