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The Lance!
4 medals, 50 points (sucks, huh?)
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TIPS -

First off, don't expect to beat the game quickly. It took me 3 generations to win it, and the champion is nearly unbeatable on the first generation.

Second, refer to the pic below if you are having trouble. It is by far the best spot, because it does a lot of body damage and is rarely covered with the enemy shield.

Try your best to juggle your mastery of items. After a short while this will likely prove impossible, but the longer you can keep at least a few items from being mastered you can rise in levels much faster. Another option would be to get an item that gives experience as its bonus, because mastery effectively becomes irrelevant.

It is possible to get both the head and the body at the same time, getting both XP, and money, for them. A little tricky, and I'm not quite sure what the precise method is, but hovering near the neckline seems to work the most often.

You can quit anytime during a duel, and you will keep your money and experience, but you will have to start from scratch on the duel the next time you load up.

A good way to defeat an opponent is to look for the lowest armor level and attack it. Lower the level the lower the HP it has. You can also lure the shield away by moving your cursor above the knight, then move it quickly down towards a targeted armor.

Finally, it's a good idea to sell armor in the inventory screen. Not only to recoup some of your lost money from them, but because you can carry only a certain number of items - This causes that problem of not being able to purchase any more armor and horses.

MEDALS -

Handle On Things - 5 points -

First guy, easy enough.

Plays Lance A Lot - 10 points -

Takes some time.

Scrooge Mcjoust - 10 points -

I got this near the start, by just waiting a few rounds before buying anything.

Horses For Courses - 25 points -

A grinding medal, pretty much. All I can say is don't try to max out your other items, and get a few items that give bonus gold. Good luck.

PICTURE -

Most of the time, the shield won't get near this point. To be safe, however, start near the head so the enemy raises his shield up, then move over to this corner. You'll get a great hit nearly every time, and in my experience the enemy usually hits the shield this way.