Some were quite famous, others had decent back stories, while some delivered infamously poor performances before leaving London Road.
Here the PT remembers 20 of them. How many do you remember?
5.
KENNY MCEVOY: Apps: 8. Posh thought they had signed the 'next Gareth Bale' when this young wide player tuned up at the start of the 2014-15 season loan, but it was soon obvious he owed his nickname to a remarkable physical resemblance to the Welsh superstar. McEvoy did score an important, albeit lucky, goal in a 3-2 home win over Mk Dons, but he wasn't very good and Spurs soon recalled him as he wasn't seeing enough action. He made just three starts and now plays semi-pro football in the Midlands. Photo: Midlands
6.
STEVE ANTHROBUS: Apps: 2. A big, strong striker who arrived at London Road on loan from Premier League Wimbledon in the 1993-94 season. He only played twice without scoring, but that was enough for him to christened Steve 'Blunderbus' by Posh fans. Photo: Midlands
7.
PETER SHEARER: Apps: 0. 'Posh sign Shearer' screamed the ET headline in 1997 and even though it wasn't Alan it was still a pretty fine signing of a midfielder who scored plenty of goals for Bournemouth and Birmingham. Unfortunately he was crocked by the time Barry Fry picked him up and spent two seasons in the treatment room only making the first-team squad three times without stepping foot on the pitch. Photo: Midlands
8.
DARREN CASKEY: apps 4. This former Spurs midfielder didn't start off with a clean slate with Posh fans when he turned up at London Road in the 2004-05 season as he'd been involved in an incident that led to a red card for Posh legend David Farrell when playing for Notts County. Farrell booted the ball at him after he'd conceded a free kick. Caskey was a class act at his best, but way past that best during his brief spell at Posh. Photo: Mick Shaw