Tottenham draw AC Milan in Champions League Round of 16

The draw for the Champions League Round of 16 took place this morning at 6 a.m. ET. Last week, I took a look at some of the teams whom Tottenham Hotspur could draw and identified some potentially noteworthy matchups.

It turns out, Tottenham drew none of those. Spurs were drawn against Serie A champions AC Milan. The first match will take place at the San Siro on Valentine’s Day, February 14, 2023.

So in terms of opponent quality representative to the entirety of the field that Tottenham could draw, Milan is... average? There were certainly worse options out there, and the easier ones (Club Brugge in particular) had their own pitfalls. Milan is currently second in Serie A behind Napoli. They finished second in Group E behind Chelsea, losing both of their matches to the Blues in the process. They’re a good team and Spurs will have to play well to advance past them. There are no easy teams once you get to this stage of the competition.

But the reality is that we have no idea what either of these teams will look like when they kick off in February. The World Cup is likely to have an outsized effect on the whole of football, and there’s also a January transfer window to anticipate before then as well. There’s a chance both teams could look very different from what they do now, so I’m hesitant to do any prognostication until closer to the date.

But maybe we can drag Joe Jordan out of retirement for a rematch with Gennaro Gattuso in the center circle at halftime. That’d be fun!

The rest of the draw was pretty [chef’s kiss] with a couple of really tasty matchups in the next round. Liverpool vs. Real Madrid? PSG vs. Bayern Munich? Love it.

Here’s the full draw.