Wolves' relegation from the Premier League has capped off a miserable spell as manager for Terry Connor.
A tearful Connor was left to rue yet another defeat as Manchester City won 2-0 at Molineux on Sunday to seal Wolves' fate.
Since his appointment as Mick McCarthy's successor in February, Connor has picked up just two points from 10 games in charge and is still searching for his first win with three matches remaining.
However, his points per game rate of 0.20 is not the worst in Premier League history.
That dubious honour goes to Jimmy Gabriel, who lost six and drew one of his seven games in caretaker charge of Everton in 1993/94.
Gabriel oversaw a miserable spell between Howard Kendall's departure and Mike Walker's appointment.
Walker guided Everton to safety with a dramatic win on the final day, when they came from two goals down to beat Wimbledon.
However, Gabriel did win his only game in a separate caretaker spell in 1990, giving him a better career record than Connor.
Connor's 0.20 points per game place him just ahead of Paul Jewell, whose Derby side went winless in 24 Premier League games under his charge in 2007/08.
So bad was their form, Jewell remarked: "The fans were singing 'you're not fit to wear the shirt', and they were right."
Next comes McCarthy's ill-fated spell in the top flight with Sunderland, who also crack the bottom 20 with Kevin Ball and Howard Wilkinson.
Les Reed, in 11th, might be the least successful manager on the list. He was appointed permanent boss of Charlton in November, but lost his job after just seven matches and has never managed since.
Alan Shearer's disastrous time at Newcastle in 2009, in which the Magpies were relegated, also makes the list.
Special mention must go to Dave Bassett and Chris Hutchings, the only men to appear in the bottom 20 with two clubs - Bassett with Nottingham Forest and Leicester; Hutchings with Bradford and Wigan.
LEAST SUCCESSFUL PREMIER LEAGUE MANAGERIAL TENURES
- Minimum six Premier League games managed.
- List refers only to the Premier League era, which began in 1992.
- Dates cover span of Premier League matches, not entire tenure.
- Statistics refer to each manager's specified tenure at a club, not their overall Premier League record.
* In joint charge with Colin Todd.
** Does not include spell in 1997 as joint manager with Stuart Pearce.
Stats from Opta