if they win the quadruple, does it straight away top the 99 treble season or are there other factors for a debate between the 2?
The quadruple would top our treble, don't see any way to argue against it.
I would say that the level of competition in both the league, FA Cup and the CL was much closer in 99. There were way more draws because there were very few dead rubber matches.
For the league in '99 we went in to the last 2 games where one of three teams could still win it. There was a really strong Leeds side who came 4th and Harry's Hammers were a strong 5th place. You compare that to this season and its Liverpool and City out on their own by a mile with the rest of the big 6 stuttering over the line, all well off the pace and no one really putting pressure on them.
In terms of the CL in '99 we had the proper group of death with Barcelona and Bayern, then Inter Juventus and Bayern in the knockouts. All those teams had world class players and any one of them could have won it.
In the FA Cup we had to beat Chelsea, Arsenal and Liverpool along the way. The final was a bit of a cake walk but thats cos we had knocked out all the big teams.
I mean its obviously because Klopp and Pep have put together such good teams but when you can steam roll your opponents for 98% of the games you play surely its significantly reducing the difficulty setting.