| Embarrassment | Player | Job |
| 4 completions, 4 interceptions in Super Bowl XII | |
| All time interception leader with 311 (34 more than next highest) | |
| 0-8 record, 11 blown saves, 7.38 ERA in 2009 season | |
| Was paid $14.7 million in 2008 for a .158 average and 3 HR | |
| Drafted #2 overall, retired with 50.0 QB passer rating | |
| Lost 1999 Open Championship despite 3 shot lead on final hole | |
| Received 73 game suspension for role in a 2004 fight | |
| 'Lost to a girl' (Billy Jean King) in 'The Battle of the Sexes' | |
| Allowed 5 goals in only period of NHL career | |
| 5 wild pitches in 3rd inning of 2000 NLDS Game 1 | |
| Ran wrong way to give other team 2 points in a 1964 game | |
| Broke own record with 40 technical fouls in 2000-01 | |