Thanks for the title change

If I understand you correctly, this formula will do what you want...
=COUNTIFS($E$3:$E$18,">=50%",$E$3:$E$18,"<=55%",$F$3:$F$18,"win",$B$3:$B$18,B23)

However, your dates in B3:B13 are 2013, but the dates you are looking for are 2014