Kenny Jackett knows firsthand the quality of youngster Pompey will face when they welcome Spurs’ under-21s to Fratton Park in the Checkatrade Trophy tonight.
The Blues boss will come up against his former employers as his current side looks to maintain their 100-per-cent record in Southern Group A.
Pompey have already beaten Gillingham and Crawley in this season’s competition, sealing their progress to the next stage.
And a win over Tottenham’s young guns would ensure they go unbeaten in the group phase.
Prior to being appointed Blues manager in the summer of 2017, Jackett spent some time coaching Spurs’ emerging talents.
He was without a job after leaving Rotherham a year previous, when the role at the Premier League outfit became available.
Jackett spent time watching and working with the club’s under-23 and under-18 sides and was impressed by what he saw.
Goalkeeper Luke McGee and Anton Walkes arrived at Fratton Park after working with Jackett during his spell at White Hart Lane.
And he believes there are plenty of others currently within the Spurs youth set-up worth keeping an eye on, who could pose a serious threat to Pompey tonight.
Jackett said: ‘I was there for six or seven months.
'I worked and watched closely with what I considered to be an excellent category one academy in terms of the standards that they set and the players that they produce.
‘I was looking at players for their first team and also players playing at different levels.
‘It was an interesting time to look slightly from the outside rather than being a front-line manager, so it was an interesting period.
'It will be a difficult game against them.
‘Looking to the last two Checkatrade games and the under-23 games, they have played in Premier League 2, the vast majority of the players.
‘And I presume they will be playing tonight.
'One of the reasons the big clubs, like Spurs, come in to the competition is to play at places like Fratton Park.
'They want to give their players the opportunity to play on league grounds against players with league experience.
'We'll see a very talented team as we did with Chelsea last season.'