Eh. Heavy damage to one of our ships constitutes enough of a "good news for their side" that this really isn't a win for us. We only have so many ships available to escort our civilian vessels, so having one of them put in the hospital for 9-12 months is a serious problem.
Basically, the outcome is close enough that we can't judge whether it was a win or a loss until we know the strategic consequences. I'd say this is a loss for us if having Challorn out of commission enables a Sydraxian raid to exploit a weakness and do damage later. I'd say this is a win for us if Ainsworth rapidly seizes the opportunity granted by the Sydraxians stopping to repair two of their ships and hits them hard in a tender spot. I'd say it's a tie if nothing major happens on either side as a result, because the casualties weren't that high and nobody actually lost a ship.
That said, note that the Sydraxian ships screamed and ran away as soon as their shields were collapsed by EXETER SMASH. This may represent a change in their rules of engagement, exactly the sort of change you'd expect if they are either one, afraid of us... or two, out of repair berths for damaged ships.
The Matthews-Rayburn Captain of the Year award is given specifically for acting to preserve redshirt lives, generally by doing something out of the ordinary. It's the collective old redshirt hands of Starfleet voting you "Best. Captain. EVER." At least for this year, and only if you did things in ways that result in minimizing redshirt casualties.
[Kirk would never, never have won this award, if it had existed back in his glory days, which it didn't, as the names of the awards show. He tried, but he just never could pull it off]
Mbeki got the 2311 award for managing to save almost the entire crew of the Miracht despite the ship taking a radical nacellectomy.
Saavik got the award one year just by putting in her log something along the lines of "I have declined to remain in a known ambush zone awaiting further developments, and am instead proceeding to Risa," which is, well, "Best. Captain. EVER."
Nash got it in 2310 for inspired safety briefings, and probably at least one other year given how good she is at keeping her crew alive.
Thuir got the, uh... 2302? award for his handling of Ulith III, and also received the more prestigious Kaplan-Mallory Award for same.
McAdams is definitely a contender, though. But the year is young, so who knows what will happen?