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Other than delving into the Fighter class for 4 attacks per action, I have found very few ways to expand your repertoire of attacks per turn to put towards a brawler build that emphasizes shoving and grabbing combatants to control the field. I had a few suggestions, Haste and the Tavern Brawler feat, commented at the time, but I'm wondering what else might be there?

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    \$\begingroup\$ Are you asking about per action, or per turn? \$\endgroup\$ – Miniman Aug 29 '18 at 4:49
  • \$\begingroup\$ Comments are not for extended discussion; this conversation about whether Extra Attack allows multiple grapple attempts has been moved to chat. \$\endgroup\$ – nitsua60 Aug 29 '18 at 11:47
  • \$\begingroup\$ @Miniman Either would work, but two attacks per round is two attempts to grapple, and if I miss one, then I'm not doing my job of holding people still, which can suck when everyone else in the party is some form of spellcaster, for example. \$\endgroup\$ – Arenn Aug 29 '18 at 16:59
  • \$\begingroup\$ By "additional attempts to grapple or shove in one action" do you mean several grappling/shoving attempts (perhaps without attacking), or a single grappling/shoving attempt in addition to your attack(s)? \$\endgroup\$ – enkryptor Aug 29 '18 at 17:06
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    \$\begingroup\$ @Arenn and why do you want several grappling attempts for this? Do you want to grapple multiple characters or just increase your chances of successful grappling? It would be nice if you reflect this in the question. \$\endgroup\$ – enkryptor Aug 30 '18 at 9:38
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There are a few different ways to go about this:

Extra Attack

Like you say, a fighter's Extra Attack lets you make up to four attacks per turn, but many classes will let you make two attacks - Barbarian, Monk, Paladin and a bunch of subclasses, which cover most brawler builds.

Haste

Haste is one of the few effects that gives you a second action on a turn, and is thus a great way to get an extra grapple attempt in. Of course, you do need five levels in a spellcasting class to get this, as opposed to the other way to get an extra action.

Action Surge

Twenty levels of fighter for four attacks is a bit much, but a two-level dip gets you this beauty. Only once per short rest, which is a bit of a bummer, but on the other hand you can use Extra Attack with it.

Tavern Brawler and Shield Master

I list these together as they both use your bonus action, but these feats (which are an optional rule, but a popular one) do provide different options - Tavern Brawler lets you grapple as a bonus action when you hit with an unarmed or improvised strike and Shield Master lets you shove when you take the Attack action while holding a shield.

Thunderwave, Gust of Wind, Entangle...

As a slightly left-field suggestion (though compatible with getting Haste), a lot of spells let you push people around or hold them in place. Thunderwave pushes a group of people back from you, Gust of Wind consistently pushes in a line, and Entangle effectively grapples a whole bunch of people. It doesn't let you make more attempts per se, but a single casting of one of these spells is equivalent to several push or grapple attempts.

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    \$\begingroup\$ Haste may not necessarily allow you to grapple, as the action it grants "can be used only to take the Attack (one weapon attack only), Dash, Disengage, Hide, or Use an Object action." A restrictive reading suggests that a grapple is not "one weapon attack" so cannot be used with the extra action from Haste. \$\endgroup\$ – Carcer Aug 29 '18 at 13:34
  • \$\begingroup\$ The hasted attack is described as "One weapon attack" with an attack action, while grapple is a "special melee attack" that takes 1 attack during the attack action. I would interpret that a melee attack is also a weapon attack with a melee weapon, since unarmed strikes are also considered a weapon. So it make sense that you could make one grapple attempt during your hasted action. The term "special" seems to leave a lot to the imagination, though. \$\endgroup\$ – Duncan Aug 29 '18 at 14:17
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    \$\begingroup\$ Even if the Haste weapon attack doesn't let you grapple, the weapon attack it provides no longer has to be spent on the Attack that does. Attack with Haste, grapple with regular. \$\endgroup\$ – 40355 says Reinstate Monica Aug 29 '18 at 17:13
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In addition to @BlueHairedMeerkat's answer:

The monk's Way of the Open Hand monastic tradition grants the Open Hand Technique feature, which allows you to shove an opponent with your attack (requires a ki point to use Flurry of Blows):

Whenever you hit a creature with one of the attacks granted by your Flurry of Blows, you can impose one of the following effects on that target:

  • It must succeed on a Dexterity saving throw or be knocked prone.

  • It must make a Strength saving throw. If it fails, you can push it up to 15 feet away from you.

The Sentinel feat allows you to stop an opponent's movement (not exactly grappling, but controlling the field in the same way):

When you hit a creature with an opportunity attack, the creature's speed becomes 0 for the rest of the turn.

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Gain advantage

Advantage essentially functions as a new chances to grapple since you roll a second d20 so a fail can be ignored. Grapples and Shoves are not attack rolls so getting advantage is different than it would be for regular attacks. Below are a few options:

  • The enhance ability spell for Bull's Strength
  • The Help action (such as from a familiar)
  • Barbarian feature: Rage
  • Inspiration
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