Pompey slumped to defeat the last time they stepped out onto an artificial playing surface.
And four members of that side from July 2016 could line-up at Harrogate Town on Monday evening (7.45pm).
It was Sutton United who provided the pre-season opposition for Paul Cook’s team ahead of a 2016-17 campaign which would yield the League Two title.
And the encounter would produce a 2-1 victory for Paul Doswell’s National League outfit.
Cook had rotated his squad for the fixture, with Christian Burgess named as skipper and Alex Bass, Brandon Haunstrup and Ben Close also in the starting XI.
Also included on the Borough Sports Ground’s 3G were Adam Barton, Ben Tollitt, Conor Chaplin, Milan Lalkovic and triallist Chris Sessegnon.
Yet the Blues would suffer a maiden pre-season loss, with Cook afterwards criticising those fringe players who had been handed a first-team opportunity.
First-half goals from Roarie Deacon – who had been on trial with the Blues earlier in the summer – and Bedsente Gomis gave the hosts an unassailable lead.
It was substitute Christian Oxlade-Chamberlain who netted an 81st-minute consolation in front of a 1,188 crowd.
More than three years later, Burgess and Close could start against Harrogate Town in the first round of the FA Cup on an artificial pitch.
Bass is on standby for injury concern Craig MacGillivray, while Haunstrup has pushed himself forward following his impressive appearance off the bench against Southend.
Pompey also suffered an Astroturf humbling in July 2012 at Gibraltar.
Michael Appleton took a squad of youngsters and triallists for 10 days in Benahavis, Marbella, while senior players remained on the south-coast ahead of their exits.
And the team slipped to a 4-0 loss in front of a Victoria Stadium crowd of 1,400, which contained a sizeable Pompey element.
The Blues side included nine triallists, plus skipper Sam Magri and his central-defensive partner Adam Webster.
They were joined by the likes of Simon Eastwood, Mustapha Dumbuya, Jon Harley, Lloyd Sam, Brian Howard and Izale McLeod.
Meanwhile, cameos off the bench were provided by Jed Wallace, Ashley Harris and Dan Butler.
It heralded a wretched season for Pompey, who remained in administration until April 2013 and suffered relegation to League Two.