When girls wink, they look really cute. These are no exceptions in the heroines of Super Sentai. They may fight evil, but they are still human ladies beneath it all. So it should come of no surprise that sometimes they'd utilize such thing during battle. This usually happened when they use their usual disguise trait, and usually when the disguise is as a Cowgirl. Sometimes, the wink serve as a finishing touch, before the enemy fall in defeat. So, here's a list of when girls wink after beating up the enemy while disguised... mostly as cowgirls.
Akira Momoi from Denziman started it when the Denziman is fighting a television-based monster, where the team got re-outfitted into cowboy/cowgirl outfits.
Later on, Miki Momozono from Goggle V does this against enemy soldiers under a monster who fights like a cowboy/marksman. She even adds up a very cute "Ufuun~" sound in the end!
In Dynaman, this doesn't happen as a cowgirl disguise, but when Rei Tachibana shed her fencer disguise, she does this for good measure.
... On second thought, I was wrong. She does eventually disguised herself as a cowgirl and winked. AGAIN.
And then in Changeman, since one girl is not enough, so two girls would suffice. So, we have both Sayaka Nagisa and Mai Tsubasa winking at the enemy. Note that Sayaka's cowgirl outfit look similar to Miki's.
I haven't watched Go Go V or Timeranger, but I heard that during their teamup movie, such event happens. In this case, just like Sayaka & Mai; Matsuri Tatsumi (GoPink) and Yuuri (TimePink) combine their wink on their cowgirl outfits.
And that's what I have gathered so far on when girls make use of winks in the middle of battle. Please do tell me more if I missed something similar. Especially when they're disguised as cowgirls since that seems to be a recurring thing in the Super Sentai series.
(And yes, the title is based on a sketch by Monty Python... Know what I mean? Know what I mean? Nudge nudge, say no more, say no more...)