Maddison impressed during City's 2-1 defeat at Manchester United last night for the Premier League's curtain raiser, before being replaced by Jamie Vardy just after the hour mark.
Spurs wound up signing nobody during the transfer window, while Reds boss Jurgen Klopp ended up signing Xherdan Shaqiri instead of the Leicester star.
But some fans of both clubs on Twitter seem to be regretting their side's failure to sign Maddison.
We’ve missed out badly on james Maddison said it from the start, perfect poch player, similar to eriksen #THFC— Finn (@finnmurphy6) August 10, 2018
Intrigued to see how James Maddison gets on this evening, despite his past tweets taking swipe at Bale/Spurs, I'm a big fan of his game, would've liked him at #THFC, as an alternative to Grealish. Looks a helluva talent imo.— Jonny Evans (@JontyEvans) August 10, 2018
Why didn’t lfc sign Maddison and Chilwell? Two players Klopp wanted and everyone doubted as usual. Proving everyone wrong, both class.— NiHADlfc (@NiHADlfc) August 10, 2018
Wish we signed James Maddison, He's just brilliant #LFC— Derrick Tello (@deero_tello) August 10, 2018
Thought Maddison played well tonight. Unlucky not to get a goal. Pity that Zac LFC lad was talking thru his arse about him joining us. He must be the biggest fraud on here. #LFC— David Lovett (@dlovett32) August 10, 2018
Tottenham kick off their Premier League season with a trip to Newcastle this afternoon, while Liverpool host West Ham United at Anfield tomorrow.
The pressure is on Mauricio Pochettino to get a good result. Anything but a victory and it will give Lilywhites fans more ammunition to throw at the Argentine and chairman Daniel Levy for refusing to bolster their ranks during the transfer window.