A winning draw is when you bat first, score more runs then the oppostion but fail to bowl them out.
A losing draw is the opposite - you've batted second and have failed to chase down the score, but you haven't conceded all of your wickets.
I used to play Northern League where we did have winning/losing draws.
I now play Palace Shield, where it's win lose cricket.
Both systems have their merits, and I honestly don't mind which I play in.
Most people hate having draws, as that's normally due to oppostition not attempting to win the game, and batting for a draw from very early in the innings, but in my opinion that should just challenge the fielding skipper to try different things in the field, and strive more to bowl teams out.
I sometimes find win/lose boring, as there's not really any attempt to bowl sides out, they just set negative/defensive fields and let Tommy Trundlers bowl negative lines, as they don't need to bowl you out, just make sure you score fewer runs than them.
Both formats can work, as long as the teams play in the right spirit