"Losing hurts more than winning feels good” has been cited in print since at least November 1986, when it was said by Portland Trail Blazers coach Mike Schuler. The saying has also been credited to baseball manager Sparky Anderson (1934-2010).

The saying means that winning is very difficult and brings temporary joy, but it never replaces all the hurt of losing.


3 November 1986, The Oregonian (Portland, OR), “Schuler notes deficit in rebounds,” pg. E3, col. 3:
“Losing hurts more than winning feels good.”
(Mike Schuler, coach of basketball’s Portland Trail Blazers—ed.)

Google Books
Ambition:
How We Manage Success and Failure Throughout Our Lives
By Orville Gilbert Brim, Jr.
New York, NY: Basic Books
1992
Pg. 30:
Some people will say, “Losing hurts more than winning feels good.

Leadership Journal
Winter 1993
ICONS EVERY PASTOR NEEDS
Six ways to remember your value.
Greg Asimakoupoulos
(...)
Someone once said, “Losing hurts more than winning feels good.” I agree. Criticism drowns out the inner joy we feel when we’re doing the best we can. It arouses the demon of self-doubt. To combat the despair that follows these daggers, I have found a way to refocus my perspective. I keep on hand icons of affirmation.

14 February 2004, The Times (Shreveport, LA), “Herd behavior can be hazardous to your wealth‎” by Diana Decharles, pg. B6:
Larry Bird, the former Boston Celtic said it best, “Losing hurts more than winning feels good.”

Los Angeles (CA) Times
Post-traumatic Iraq syndrome
The war is lost. Americans should begin to deal with what that means.
By Christopher J. Fettweis
June 12, 2007
LOSING HURTS MORE than winning feels good. This simple maxim applies with equal power to virtually all areas of human interaction: sports, finance, love. And war.

Google Books
Losing Hurts Twice as Bad:
The Four Stages to Moving Beyond Iraq
By Christopher J. Fettweis
New York, NY: W. W. Norton & Company, Inc.
2008
Pg. 27:
The next theme of this book echoes Sparky Anderson: Losing hurts more than winning feels good.

SBRforum.com
Boston Red Sox & Rays prove MLB comebacks offer go-against spots
Monday, July 04, 2011 12:00 AM ET
(...)
You may have heard the old sports axiom, “Losing hurts more than winning feels good.” Professional athletes often can’t wait to get back on the field after a frustrating, heart-breaking loss to atone for the previous night’s sour ending. Other times, teams off thrilling comeback wins can be flat. All of which can make for a potential sports betting go-against the next game.