I let my pup win all the time, it's good for them to gain confidence! Don't set a pup up for failure.She gave me a work book and its in there. She didn't tell me this. Had she, I would've asked her directly.
My girl is a Lab/Mastiff mix. Sometimes she wins and sometimes I let her. But either way she immediately puts it back in my lap - so I don't think she cares or even realizes she "won". When I win, she sits and I throw it. Seems harmless.