He did, and quickly gains the upper hand! But he might have gotten cocky!

As Raynare approached swiftly, Issei lurched. She was still faster than him, but not so much she could blitz him without him being able to respond. The spear missed, and she blinked, and was so surprised that he dodged, that she couldn't avoid his retaliation in the form of a kick, right in her solar plexus. "Ugh?" she grunted, skidding back. "What the hell!?"

Issei immediately started moving to gain som distance, getting out of the house and into the yard. "Whew, that was close!" he said, not even faking his nervousness. She had in fact almost had him.

"...okay, you're better than I thought," she grunted, straightening up and rubbing her smooth abdomen, wincing in discomfort. "Alright then, let's see how you handle THIS speed!" She charged him again, considerably faster than before, clearly not messing around anymore, and quickly closing the distance.

"Boost!" Issei yelped. And he had triggered it just in time, as Raynare's speed seemed to halve just as she was on him, as his perception doubled. He ducked her spear, his scalp being grazed, and the holy light making an intense burning sensation spread through it, making him wince, but he pushed through, and came back up, uppercutting Raynare.

She cried out, staggering back, and holding her chin, which was already starting to bruise. "What!?" she demanded again.

"Damn it, you messed up my hair!" Issei whined, patting the smoking strands, which, sure enough, were now missing a strip. He made a mental note to have Rias fix that later.

"You son of a bitch!" Raynare roared in a rage, and began forming more javelins, and rapidly hurling them at Issei.

"Shit, she's spamming!" Issei yelped as he began frantically dodging, and Raynare smirked, redoubling her efforts. "Boost!" he intoned again as the barrage continued.

This continued long enough for Issei to activate yet another boost, now making dodging all of Raynare's spears almost easy. "That all you got!?" he taunted, hoping to get her furious, and sloppy.

It proceeded to backfire as she snapped, and she threw a spear into the ground, and it exploded, sending Issei tumbling as he lost his footing. "You're mine!" Raynare shouted, dashing at him, another spear raised to end him as he fell.