“There are a thousand ways to lose a horse race and only one way to win” is an old horse racing adage. “Jim Fitzsimmons has contended for many years that there are 1,500 ways to lose a race honestly” was cited in 1925. “There are many, many ways to lose a horse race” was cited in 1930.
 
“There are 85 different ways to lose a horse race, but only one way to win—to get there first, barring disqualification” was cited in 1936. “There are 50 ways to lose and only one way to win” was cited in 1939. “There is only one way to win a horse race and there are 10,000 ways to lose one” was cited in 1940.
 
   
3 November 1925, Biddeford (ME) Daily Journal, “White Flakes Caused Nag to Lose Race,” pg. 7, col. 4:
Jim Fitzsimmons has contended for many years that there are 1,500 ways to lose a race honestly, but it seems as if there were twice that many different excuses presented for this year’s bad races.
 
16 May 1930, Logansport (IN) Pharos-Tribune, “The Sportlight” by Grantland Rice, pg. 10, col. 3:
Gallant Fox is a heavy favorite, but as Mack Garney says, there are many, many ways to lose a horse race.
   
27 March 1936, Salt Lake Tribune (Salt Lake City, UT), “Sports In Retrospect” by Jimmy Hodgson, pg. 18, col. 1:
Rose Ben, a well-known handicapper, stopped in on his way to New York to tell us that there are 85 different ways to lose a horse race, but only one way to win—to get there first, barring disqualification. And still some guys think they have chance to beat the ponies!
 
19 July 1936, Seattle (WA) Sunday Times, “Hawkeye,” pg. 14, col. 6:
A thousand ways to lose a bet,
But just one way to win—
The Hawkeye way, the best way yet,
It brings your horses in!
 
11 November 1939, The Oregonian (Portland, OR), “Webfoots Picked to Defeat Beavers in ‘Civil War’ Tilt,” sec. 2, pg. 2, col. 3:
As race-horse men say, there are 50 ways to lose and only one way to win.
 
2 May 1940, Charleston (SC) Evening Post, “Today’s Sport Parade” by Henry McLemore (United Press), pg. 2B, col. 8:
There is only one way to win a horse race and there are 10,000 ways to lose one.
 
The way to win it is to be there first. The ways to lose it take your choice: Bad jockey, bad start, bad pockets, bad tracks, bad judgment of trainers or owners, and all the other bads you can conjure up.
 
Google News Archive
8 February 1941, Miami (FL) Daily News, “Mioland Will Win Santa Anita Stake, Says Jockey Haas” by Henry McLemore (United Press), pg. 2B, col. 2:
“No one ever stops to think that there are 99 ways to lose a race and only one way to win one.”
(Leon “Buddy” Haas, a jockey.—ed.)
 
Google News Archive
18 December 1971, Daytona Beach (FL) Morning Journal, “Ticker Tempo,” pg. 17, col. 1:
“Nobody gets rich betting the horses. You got ninety ways to lose and one way to win.”
—Nathan Detroit in Damon Runyon’s “Guys and Dolls”
   
Google Books
Chronicle of the Horse
Volume 41, Issues 14-26
1978
Pg. 3:
“There are a thousand ways to lose a race,” the Gaekwar of Upperville (or someplace) once said, “and only one way to win it.”
 
Google Books
Mister, You Got Yourself a Horse:
Tales of Old-Time Horse Trading
Edited by Roger L. Welsch
Lincoln, NE: University of Nebraska Press
1981
Pg. 190:
A little protection, I thought, as there is a thousand ways to lose a horse race and only one way to win one, and that is to get under that wire first.
   
Google Books
India Today
Volume 9
1984
Pg. 84:
As Cyrus Madan, editor of Turfite, the only racing periodical in the country, says: “There are a dozen ways to lose a race but only one way to win.”
   
Google News Archive
11 August 1996, The News (Boca Raton, FL), “Loss was inevitable, even for Cigar” by Vic Ziegel (New York Daily News), pg. 5D, col. 1:
A few minutes after the race was over, Jerry Bailey, Cigar’s splendid rider, reminded us of the-old racing line. “A thousand ways to lose,” he said, “and only one way to win.”
 
Tampa Bay (FL) Times
At the Tampa Bay Derby, racing superstitions are common (horse) sense
Susan Thurston, Times Staff Writer
Thursday, March 10, 2011 1:23pm
(...)
“There are a million ways to lose a race and only one way to win it — get there first,’’ wrote Mellul, who represents two jockeys at Tampa Bay Downs on his blog, the Hustling Book (hustlingbook.blogspot.com).
 
The Times-Picayune (New Orleans, LA)
Large fields, inexperienced horses can lead to long-shot winners in big races
By Katherine Terrell, NOLA.com | The Times-Picayune
on March 26, 2013 at 4:22 PM, updated March 26, 2013 at 5:00 PM
(...)
And as the saying goes, there are at least 1,000 ways to lose a horse race and only one way to win. Horses can be the victim of pace, throw a shoe (as Mucho Macho Man did in the 2011 Louisiana Derby), have a bad trip, or any number of issues.
     
Boston (MA) Globe
Bob Neumeier has a rooting interest in Triple Crown
By Chad Finn GLOBE STAFF JUNE 05, 2015
It’s about the race for Bob Neumeier, always has been. A respected Boston sports anchor and host for decades, Neumeier — better known as Neumy to, well, everyone — long ago established a parallel profile nationally built in part around his expertise in horse racing.
(...)
“Would I like to see a Triple Crown? Absolutely,’’ said Neumeier. “Who wouldn’t? We haven’t had one since ’78 and we’ve had a lot of great horses come up and down the road. But there’s an old racetrack saying that there’s one way to win and 21,000 ways to lose. That’s racing.”