Milan's winter of discontent could lead to Champions League cheer for Tottenham

The Champions League restarts next week with the first four matches in the round of 16 and it is interesting to reflect on how much has changed since the draw was made in the autumn.

Pundits' assertions that 'this is a good time to be playing Team X' should generally be treated with suspicion – especially as it's often uttered after, rather than before, the game in question.

But it is relevant at this stage of the Champions League given all the injuries, transfers, managerial changes, fluctuations in form, behind-the-scenes bust-ups and off-field scandals that might have occurred between the last-16 draw, which this season took place on November 7, and the ties actually kicking off. 

What appeared to be a stinker of a draw in November may, by the start of February, resemble a virtual bye to the quarter-finals so punters' noses ought to be twitching at even the faintest whiff of a stale price in the 'to qualify' betting or outright markets. 

Bookmakers were struggling to pick a favourite when Tottenham were paired with Italian champions Milan in the last-16 draw but Spurs are as short as 4-7 to progress after the Rossoneri's dismal start to 2023.

Last Sunday, shortly after Tottenham had beaten Champions League favourites Manchester City 1-0 in the Premier League, Milan lost by the same scoreline to derby rivals Inter.

The 1-0 margin flattered the losers, who didn't have a shot on target and had been beaten 5-2 by Sassuolo and 4-0 by Lazio in their previous two Serie A matches. Milan's post-World Cup woes also include a Coppa Italia defeat to Torino and a 3-0 Italian Super Cup rout by Inter so the plunge on Tottenham looks well founded.

The injury to first-choice Spurs goalkeeper Hugo Lloris might have offered a glimmer of hope for Milan, if not for the fact that their own French international custodian Mike Maignan is also sidelined.

Another player who will be absent for the round of 16 is Chelsea striker Pierre-Emerick Aubameyang, who was left out of the Blues' Champions League squad to make way for a host of new signings.

Aubameyang, now reportedly eyeing up a loan move to MLS, is still available at a not-very-enticing 100-1 to be this season's top Champions League goalscorer and his former club Borussia Dortmund should go into their last-16 clash with Chelsea in good spirits. 

At the time of the draw, when Mykhaylo Mudryk, Enzo Fernandez and Joao Felix were still just twinkles in Todd Boehly's eye, Dortmund were struggling in the Bundesliga. 

Since the winter break, though, Edin Terzic's men have won all five of their league and cup games, scoring 16 goals – 13 more than Chelsea managed in their first seven matches of 2023.

Paris St-Germain are missing the injured Kylian Mbappe for the first leg of their heavyweight clash with Bayern Munich, Liverpool are at a low ebb for the repeat of last season's final against Real Madrid, but Eintracht Frankfurt are going well in the Bundesliga. Unfortunately for them, they face a rampaging Napoli side who are 13 points clear after just 21 games of the Serie A season. 

One of the less glitzy last-16 ties is also full of intrigue. Benfica have lost World Cup-winning midfielder Fernandez to Chelsea in January but their tie against Club Brugge is looking increasingly peachy.

In the autumn, the Belgians were the toast of Europe – or the toast of Bruges, at least – after stylishly qualifying from Group B at the expense of Atletico Madrid and Bayer Leverkusen. However, they went into Friday's fixture against Union Saint-Gilloise having won only once in nine Belgian Pro League matches since the start of November so – and I don't say this lightly – this may be a good time to be playing them.

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