What are you using it for?
Here's some things to consider:
In my experience: Speakon NLT4 connectors are physically able to accomodate up-to 10 gauge wire, although you'll need to use an SJ type cable to keep the OD down small enough to physically fit into the end of the barrel.
In my experience: Speakon NL4 connectors are physically about to accomodate up-to 11 gauge wire. The NL4FX requires SJ wire on heavier gauges. NL4FC will accomodate SO wire up-to 12-4.
In my experience: I don't advise lashing up 1/4" phone plugs on anything much heavier than 13 ga., and even at that, I recommend G&H Megafoot ends of similar heavy duty end. Standard Switchcraft No. 280 Phone Plugs won't accomodate cable much heavier than 16 ga. The heavier cables and 1/4" plugs typically put too much strain on the panel jacks and can cause problems there if you don't strain relief the connection.
In my experience: Typically, Banana plugs accomodate up-to 13 ga. fairly well. There are Banana plugs that will accomodate considerably heavier gauges, but typically they're not common.
In my experience: Amplifier 5 way binding posts are typically built to accomodate up-to 12 or 13 ga. wire through the hole.
There's an opinion by some that large gauge cables might knock the high frequency possibly. Other folks believe thinner gauge cables effect the low frequencies. Personally, I have conducted listening tests and I believe there is a very slight difference; however, for most SR applications, it's far from significant, on either the high frequencies, or the low frequencies.
All-in all, I'm of the opinion that it doesn't make a lot of sense to equip with significantly heavier gauge cables than what it takes to do the job. It makes no sense to me to run 10 ga. cables 10ft. to a 100 watt compression driver, when 14 ga. will do the job just fine. The physical complications and cost considerations of running "over-kill" cables outweigh what little possible preformance might be gained. However, when it comes to preforming musicians, there is the "binky factor" where-in if something gives a musician more confidence, then they will play better even if it's a placebo. People really do hear with their eyes... and something that looks like it sounds good, generally does sound good.