What are some examples of sports records where the person or team that holds the record probably isn’t particularly proud to do so?
I couldn’t find any specific examples, but I’m thinking of things like most career losses by an NFL quarterback or MLB pitcher, most interceptions thrown, lowest batting average, lowest shooting percentage, etc etc.
The Dodgers’ Willie Davis committed three errors in Game Two of the 1966 World Series, all in the fifth inning, setting a Series record
Malcolm Nash, of Glamorgan, was the first first-class bowler in cricket to see every ball of an over hit for the maximum 6 runs.
Not many people know that Nash was nearly the recipient of the next maximum over. In 1977 he hit he concededr 6-4-6-6-6-6 in a single over bowled to Frank Hayes of Lancs.
But I do. 
In Gaelic games - hurling and football - there are a few counties which have never won an All-Ireland title. Both date back to 1887, making it an ongoing 118-year losing streak.
For example, Westmeath have never even reached an All-Ireland final, whereas London managed to get to 3 Hurling and 5 Football finals at around the turn of the 19th/20th Centuries (a London “selection” side won the 1901 Hurling title).
Well, the Buffalo Bills are probably not particularly proud of losing four consecutive Super Bowls.
I think it will be difficult to find individual records for ineptness that span a career because a useless sportsman will not compete at the highest levels for very long.
There is the case of a player who is on a team for particular strengths which are not relevant to all aspects of the game. For example I would imagine that most baseball pitchers have dismal batting averages (same goes for cricket bowlers).
Chess Grandmaster Fritz Saemisch once lost all 13 games of a tournament. There are worse performances, but his unusual achievement was to lose every game by exceeding the time limit.
Not so much something that he won’t be proud of, but something that must be a source of frustration for him, Australian leg-spinner Shane Warne has scored more test runs than any other player without scoring a century.
The St. Louis Blues have 25 years of consecutive playoff appearances (iirc) but have never won the cup. Always the bridesmaid…
Adam Dunn has the single season record for most strike outs (by a batter).
The Orioles have the record for the most consecutive losses to start a season (21?).
And to rub salt into the wounds about 12 months after he was out for 99 caught in the deep, it was revealed that the ball that dismissed him was a no-ball (illegal delivery) and he really should have ambled through to make 100.
A lot of ignominious career baseball records are held by pretty good players by virtue of their longevity. Case in point, the most career losses record is held by Cy Young (316), who also has the most career wins. The record I turned up for single-season losses by a pitcher is John Coleman of the 1883 Phillies, a staggering 48. Not sure what the post-1900 record would be, but surely nowhere near that.
Most times grounded into a double play-- career: Cal Ripkin Jr (350); season, Jim Rice, 1984 (36).
The 1962 New York Mets still hold the record for losses in a season (120), although the Tigers came close (119) a few years ago. Unless you count the 1899 Cleveland Spiders, who went 20 and 134.
The losingest baseball francise is the Phillies, who became the first to top 10,000 total losses recently.
Clemson’s men’s basketball team has never won in Chapel Hill against North Carolina. Currently 0-51.
Yeah, but Met fans are quite proud of that record, even rooting for the Tigers so that they wouldn’t beat it. Met fans are also proud that they are the oldest franchise never to have pitched a no hitter.
The Philadelphia Phillies has 16 consecutive losing seasons (1933-1948), a baseball record.
SS Joe Sullivan made 106 errors for the Washington Senators in 1893!
Kerry Collins fumbled the ball 23 times for the NY Giants in 2001!
Rasheed Wallace earned 41 technical fouls and was kicked out of 7 games in the 2000-2001 season!
All records
Well, during my years as an undergrad at Columbia, we set what was then the record for consecutive losses by a college football team.
Thank God for Prairie View A & M, a Texas college that erased our record! (It will take some doing to surpass Prairie View for consecutive losses.)
As others have mentioned, in MANY cases, star players hold the record for bad things. Let’s face it- a HORRIBLE pitcher isn’t going to stay in the major leagues long enough to rack up too many losses.
I mean, if a pitcher goes 3-21 in my rookie year, he probably won’t HAVE a sophomore year! The only way to amass 200 career losses is to pitch very well, well enough to have a long career.
Some “embarrassing” records are held by superstars, precisely because these records required longevity. Baseball examples:
Who has been caught stealing more times than any other baseball player? The greatest base stealer of all time: Rickey Henderson.
Who struck out more than any player in baseball history? Reggie Jackson, a Hall of Famer with 5 World Series rings.
What pitcher threw the most wild pitches and issued the most walks? Nolan Ryan, who also struck out more batters than any other pitcher.
What pitcher beaned the most batters? Walter Johnson, one of the greatest pitchers of all time.
What pitcher gave up the most home runs? Robin Roberts, a Hall of Famer.
Football examples:
Who holds the record for career fumbles?
What quarterback threw the most career interceptions? Not surprisingly, a guy who played until he was nearly 50: George Blanda!
What quarterback was sacked the most times in his career? John Elway, who took his team to 5 Super Bowls (he’s also 3rd in career fumbles).
Oops- sorry. The answer to #1 is Warren Moon, who was a very solid quarterback.
Now, if you want to stick to genuinely embarrassing records, look at poor George Frazier.
If you don’t remember George, he was a pretty good middle-innings relief pitcher for the Yankees. He lost 3 games for the Yankees in the 1981 World Series.
There’s good news and bad news for George. First the good news: he isn’t the ONLY pitcher to lose 3 games in a single World Series. Eddie Ciccotte of the White Sox lost 3 games in the 1919 World Series.
Now the bad news: Cicotte took money from gangsters to lose on purpose.
Poor George Frazier is the only man to lose 3 World Series games unintentionally!