#6 Liverpool marching towards the 2019-20 EPL title
Liverpool's early-season surge to the top spot in the Premier League has hurt Manchester United. Sure, they might not get to lift the trophy until 2020, which is technically the next decade; but with such a huge, - some-might-say - 'insurmountable' gap at the top between them and Manchester City, it seems certain that Klopp's world champions are poised to make the 2020s an era of dominance all of their own, kickstarting things by winning the Premier League in a few months.
For United fans, this is a real low: literally, the worst possible way to end one decade and begin another. Liverpool's dominant win over the Red Devils at Anfield will have done little to alleviate the gloom back across the M62.
#5 The Paul Pogba to Real Madrid transfer saga
When Jose Mourinho managed to tempt Paul Pogba back to The Theatre of Dreams in 2016, most thought it would serve as a catalyst; that Pogba would tattoo the famed badge across his chest, galvanize the talent in the dressing room, perform, and drag United back towards the summit of the Premier League, where they belonged. How wrong they all were...
Pogba has been inconsistent at best since his return to Old Trafford four years ago. The talented Frenchman flatters to deceive, all too often following up spells of good form with woeful, unspirited performances that leave a sour taste in the mouth.
Fallouts with Mourinho seemed to be happening with regularity during the 2018-19 season, with Mourinho going so far as to call Pogba 'a virus' during a dressing-room beatdown, following an abject display against Southampton in the league.
The fans sided with Pogba, and Mourinho was told to sling his hook. You could forgive those same fans for expecting their club's biggest asset to be thankful for their loyalty; perhaps to even pay them back with some increased efforts out on the field...
Wrong: Pogba played well for about 6 weeks and then slipped back into his ball-greedy, sulking ways as he and the rest of the squad limped into an embarrassing 6th placed finish.
Not a single fan was surprised come the summer when Pogba began to flirt with Zinedine Zidane's Real Madrid. The only shock came when Woodward and Co. refused to do business with Los Blancos, instead deciding to keep an unhappy player on the books for another season.