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I practice early medieval (Viking) style semi-contact as a hobby. With blunt steel weapons not with some LARP crap. I can tell you how we deal with an enemy with a shield and then some historical methods I know. Now our fights are not entirely realistic, they don't devolve into fierce unarmed struggles, at the end, where we attempt to scratch out eyes and bite. Additionally, an enemy is "dead" after one hit. This too is unrealistic as there is an important difference between the stopping and killing power of a weapon. Beeing mortally wounded and still fighting on for some time was a common thing and truly problematic. There is an account of a rapier duel where both combatants pierced each other about a dozen times until they both dropped dead. This is bad for obvious reasons. You want to take out the other guy while stopping him from taking out you. You don't want to stab a sword through his belly that he does not notice in his adrenaline rush. It might get stuck and now you are unarmed in close melee distance to a guy who is still armed and combat-capable for a few more seconds. With that out of the way, the following list will go through your weapon setup and detail the options you have. I'll assume the shield-bearer has a round shield and a Viking age sword. Techniques might vary if the defender wears some other kind of shield.

• one-handed sword Be quicker. A shield has to be used actively. It does not give you a magical defense. If you don't know how to use a shield you are better off in a fight without it. Move in slowly and just smack his head. It sometimes startles even experienced opponents. Grrab his shild with one hand and open it. Alternatively going for the head only to let your sword glide down the side of the shield to get the legs is one of my favorite maneuvers. As for "an opponent worth his salt" I manage this against my trainer, a fighter with 20+ years experience about 10% of the time. Getting lucky is always an option.




• one-handed sword and ax This is one of the few sensible dual-wielding setups. Why? The ax hooks open the shield and you thrust into the opening. You will usually win the thug of war as your opponent gets slightly startled and you got Archimedes on your side. Though this is much easier against handheld shields than against those bound to the arm.




• one-handed sword and shield Now you got the same setup as your opponent. The options from the one-handed section still apply. Other options like using your shield to block the enemy's sword between the shields or between your armor and shield are now available. A friend once oven showed me a technique where you either give up the sword or your arm gets broken. Actively using the shield is also an option. Either straight into the face to inflict damage, against the enemy shield to open it or as a feint. Bonus point for style if you throw away your sword, in the end, bash him to death with the side of the shield. It's way bloodier.




• two-handed sword (longsword) Firstly everything from the one-handed sword applies. Secondly, the ground rule for dealing with two-handed weapons as a lone shieldbearer (battle-line is way different and beyond the scope of the question) is to run them down. The long weapon will have more range, mobility (due to the greater leverage two hand offer) and deal more damage. Thus you "untersschreitest die Mensur", the fancy German way for saying you must move into a distance the enemy weapon is no longer effective and you can bash the crap out of the enemy. They of cause know this and will attempt to retreat and kill you while running backward. It's quite effective and usually, the shield-bearer wins, but not always. If the long weapon-user has a backup short-word or dagger, giving up the long weapon for it can also be very effective. this is true for all the following long weapons.




• spear High-Low, Low-High is the doctrine. Go for the face and then for the feet. Your spear is faster because of leverage. If he doesn't rush you, you'll eventually find a gap.




• Dane-axe See spear. Additionally, you can split the shield. This happens even with blunt Dane axes so a sharp one will be even more efficient. Hooking is also an option. Open up the shield, thrust the blunt tip of the axe into his face and kill him while he recovers. Or hook his knee and throw him down.




• polearm See Dane-axe. Polearms are the best weapons there are. Hence their popularity in the middle-ages.




• spear and shield Useful combo. You sacrifice the leverage of the spear for a lot of protection. This was the setup of most classical armies for a reason.




• axe and shield The lone one-handed axe sucks for defense but is amazing for offensive maneuvers. The shield... Well, it is a simple and dangerous combination and will help you deal with the shield-bearer easily.




• full plate armor I'm gonna get medieval on your arse. This is not quite medieval, but renaissance. Get a set of full plate armor, laugh about how he fails to injure you, grab his shield and sword, give him a headbutt and kill him. Should you doubt the effectiveness of full plate armor, google half-swording a set of sword techniques which was developed as a response to it.




• dagger You are screwd. This is only slightly better than bringing a knife to a gunfight. A dagger should only ever be your last backup weapon.




• incendiary grande Throw a Greek fire grenade at him or dirt or stones. Distract him with some sort of projectile and then land your blow while he is distracted. Works ver well.




• javelin The Romans used special javelins which got stuck in their enemies shields to weight them down and fore the enemy to drop them.

Traditionally one dragged the shield out of alignment using the edge of their own shield, if you're using a sword but have no shield then there are two possibilities:

• You are using a two-handed weapon, a polearm or a sword like the Zweihänder in which case you have a reach advantage and actually can simply pound your opponent until they give you an opening while trying to get close enough to retaliate.




• You are using a one-handed weapon you don't have reach advantage but you do have a free hand, you will be wearing gauntlets, grab the shield and pull. FYI you can actually pull the same stunt with your opponent's sword if you're wearing the right kind of gauntlets and you're fast enough (especially if they're using a single edged blade) but it's a good way to lose fingers if you get it wrong.

There are various relevant old jokes, such as "if you want to get there, don't start from here", or perhaps suggestions to avoid entering into an arse-kicking contest if you only have one leg.

Given that you've got yourself into this mess already, my first thought would be "distract my opponent so my friend can stab him in the side". If you've managed to get into a fight with a better equipped opponent and failed to bring a friend (and seriously, at this point you should be reconsidering your career) the best approach may be just to run away (or "make an expedited retrograde manoever" if you find the idea of running away to be distateful). You're probably less encumbered than your opponent is; put some distance between you and them, find some terrain that you can use to your advantage.

No friends, can't run away? Oh dear, oh dear.

Did you bring a side-arm? Something like a pilum would be ideal, though they are perhaps a little large. A francisca might also go down well, and there have been reports of them being used to break shields. Other smaller and lighter throwing weapons are unlikely to help, especially against larger shields.

No side arm, no friends, no escape?

The proximal cause of death at this point is likely to be stupidity, but you may yet escape if you're lucky. This is going to rely on your opponent being inept (a dangerous gamble), or being less fit than you (ie. the tiring out that you wanted to avoid) or you levelling the playing field by removing either their weapon or their shield from play without getting killed yourself (challenging, even against less skilled opponents). Frankly, I don't fancy your chances.

But enough changing the subject.

I'd like to go one up on Ash's perfectly good answer and suggest wearing a good suit of armour and wrestling.

This isn't an unreasonable tactic, after all heavy armour can be pretty difficult to get through with hand weapons. Techniques like half-swording are already important in that situation, and necessarily bring you closer to your opponent, so your poorly-equipped attacker might reasonably already be quite familiar with getting very up-close-and-personal. Parry or bind your opponents sword, and chuck yourself on them before they can bash you out of the way with their shield. Once you've got into a good struggle snuggle, the shield will go from being a useful bit of defensive kit into a serious hinderance.

You might be able to apply the same technique if you were poorly armoured, if you were desparate. Again though, I don't fancy your chances.

Using the same approach used by sports, where the defending team is actuating a solid defense, the key to break the wall is: keep trying and feinting until the defender leaves an opening.

In basketball the attacker keeps moving the ball around, same in soccer. In chess or in box the attacker prepares attacks trying to weaken the defender position. And so on and so forth.

Don't forget the saying

the threat is stronger than the execution

Just because you have a sword, you have already an advantage: you can feint an attack, but the shield bearer cannot feint a defense. It's either defend or take the blow.

With the proper combination of movements it is possible to force the defender to leave an opening and then strike.

Repeat until necessary.

(if you have anything which can obstacle the defender movement, that is even better: throw a row or a net on the ground, and let he stumble in it while dancing with his shield to block your feints)

i suggest use axe its the weapon specifically to break shield it can also hook the shield. (here an image how to hook the shield to the side)

if the user must use sword this falx sword can deal shield and cut the enemy limb (depend on the shield type since real scutum is thin) or hook the shield too.

https://en.wikipedia.org/wiki/Falx

here some example image from quick google (dont know the real source is) it force roman to wear special arm guard just to deal with the dacian falx men.

also falx and 2H axe like halberd or dane axe can just reach around ignoring the shield to cut or hook the person exposed side directly like head,neck,arm,leg, or other body side not covered by the shield.

Besides the ideas put forth already, from fighting in the SCA there were three methods of dealing with a shield, besides brute force or lightning speed

1) As has been put forward, kick or strike the outside of the shield of great force, prying open room for an attack on the inner edge (nearest the yielders center line)

2) strike the inner edge of the shield, pushing it in, which causes the outer edge to provide less protection for the side and back. Then attack, using a long weapon, at the backside of exposed side or back. You are reaching around the shield when you do this.

3) Faint and cause the defender to raise the shield to protect their face, and then time the real attack for your backswing or the spin the sword technique in your hand (forget the proper name) when they will lower their shield to get a look at what you are doing.

All attack methods have counters moves. And those counter moves have counter moves.
In the end, between skilled fighters, it's about using combinations of tactics to force the other guy to make that final mistake.