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Waiting hurts my soul...
Some guesses

Quote from charleon:

I ahd High hopes for the titles! but no, I sadly don't think it's those games. i remember the graphic to be a little bit more advanced, also from looking at youtube at castles and castles 2 the battles wasn't topdown but a more isometric perspective? The battle map in the game I can remember could be like 9x9 screens big with a castle in the middle and your characters started at the bottom of the map and moved upwards to try and infiltrate it.


http://www.mobygames.com/game/windows/lords-of-the-realm-ii/screenshots/gameShotId,147796/

Quote from bmn:
Trying to remember an old DOS shareware game from around '92 or so. It's a game in the vein of Mario Party (you have a board, roll the dice and move that distance), where a set of characters similar to those in Wacky Races (including a Dick Dastardly-like bad guy who follows you around messing you up) start off somewhere in Europe and have to get to a random location first. If I remember right you start off around London and have to get to somewhere around Germany in the first round. When your turn finishes, there's a notification that pops up that either helps you out or hurts you.


http://www.mobygames.com/game/dos/bush-buck-global-treasure-hunter
Borderlands 2 Glitch Hunter/ router.
Quote from ZenicReverie:
Quote from bmn:
Trying to remember an old DOS shareware game from around '92 or so. It's a game in the vein of Mario Party (you have a board, roll the dice and move that distance), where a set of characters similar to those in Wacky Races (including a Dick Dastardly-like bad guy who follows you around messing you up) start off somewhere in Europe and have to get to a random location first. If I remember right you start off around London and have to get to somewhere around Germany in the first round. When your turn finishes, there's a notification that pops up that either helps you out or hurts you.


http://www.mobygames.com/game/dos/bush-buck-global-treasure-hunter


this could also be Dr Drago's Madcap Chase

I played this alongside Samurai Shodown II for a little bit. It was a PC game where your character was a guy wearing black stormtrooper-like armor, but with no helmet, had a sword and also guns and had to kill 2-legged walkers that looked like AT-STs but with a longer head like Alien Xenomorphs have. You had regular enemy guys to kill too (they had armor just like you did), not just the walkers. At the beginning of the level, you were dropped from a futuristic chopper in a dark urban looking area and just side scrolled killing enemies until the final. You had to climb buildings too.

The boss for the first level was a bigger walker, crouching and firing round plasma blasts at you, he occupied almost all the right side height & about 1 third of the length, you had to jump to avoid his blasts and fire at him or get close to slash with your sword.

I think your character was a cop actually, but I'm not sure. It was from the 90s, it required something like Pentium II to play. Resolution was something like 640x480. Maybe lower like Diablo 1's 320x240, but not sure.

An example that looks like mine but it's not is here: https://i.ytimg.com/vi/0g44DCgPN-8/hqdefault.jpg . This kinda looks like the end boss stage for level 1, except the caracter is blue & vividly colored, mine was dark & noir. And the boss was a walker, had crouching legs, here is just a transport. But you get the idea.
Found mine in the meantime, it was Zyclunt - Blade Warrior. the first level
I played this game on pc in the 2000s.

This game is a single screen 2D puzzle game with many levels.

The art is very simplistic cartoon. You are this red dude with a hat trying to get to the ladder to get to the next level.

There are obstacles. I remember you can eat mushrooms and the oddly coloured mushrooms are poisonous.