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Next six games including AC Milan & FA Cup after Leicester loss

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Tottenham proved their own biggest enemy again as they followed up a rousing 1-0 victory over Manchester City by losing 4-1 at Leicester on Saturday afternoon.

Spurs seemed to re-enter the Champions League conversation with that victory over City but presented Manchester United and Newcastle with the chance to move further ahead in the top four chase by being dismantled by the Foxes.

It’s poor timing with games in both Europe and the FA Cup on the horizon in what will be a season-determining few months for Antonio Conte and co.

Here’s who they have coming up soon on their fixture list.

On this edition of OWAN, Sean Walsh & Jude Summerfield discuss record breaker Harry Kane at length after he became Tottenham’s record goalscorer. If you can’t see this embed, click here to listen to the podcast!

Gennaro Gattuso, Luka Modric

Spurs and Milan squared off in 2011 / Alex Livesey/GettyImages

It’s crunch time in the Champions League as Spurs are next in action when they travel to San Siro to take on Italian outfit AC Milan.

The current Serie A champions have been terrible since club football resumed after the World Cup but did snap a run of seven games without a win by beating Torino.

Jarrod Bowen, Ivan Perisic

Spurs and West Ham drew earlier in the season / Marc Atkins/GettyImages

After the first leg of their last 16 tie, Spurs host West Ham in a London derby at Tottenham Hotspur Stadium.

The earlier fixture between the two sides this season finished 1-1 as Tomás Soucek grabbed the Hammers a point following Thilo Kehrer’s own goal.

Thomas Tuchel, Antonio Conte

There will be no round two between Thomas Tuchel and Conte / Marc Atkins/GettyImages

It was a fiery London derby between Chelsea and Spurs at the start of the season when Conte’s side emerged with a point after Kane’s late equaliser.

He’ll be facing Graham Potter in the Blues dugout, however, as well as a number of blockbuster January signings.

Billy Sharp

Sheffield United eventually saw off Wrexham / Michael Regan/GettyImages

Tottenham remain in the hunt for domestic silverware through the FA Cup but have been handed a dicey trip to Championship promotion hopefuls Sheffield United.

The Blades needed two legs to beat National League Wrexham but haven’t lost since November and will definitely fancy their chances of springing an upset at Bramall Lane.

Harry Kane

Kane scored in a 1-0 win over Wolves in August / Visionhaus/GettyImages

Wolves have given Spurs the runaround on a number of occasions since their promotion back to the Premier League in 2018, but Tottenham have a good recent record when visiting Molineux.

They’ve won five of the last six meetings at Wolves’ stadium, including a penalty shootout victory in the Carabao Cup when Nuno Espirito Santo was in charge in September 2021.

Tottenham Hotspur v AC Milan - UEFA Champions League

Spurs celebrate their 2011 triumph over Milan / Jamie McDonald/GettyImages

With the first leg still to be played, Tottenham could need all sorts of results when they host AC Milan in the second game of their last 16 tie.

In their 2010/11 meeting, Spurs secured progression to the quarter finals with a goalless draw at White Hart Lane having won 1-0 at San Siro. They’d definitely take a similar result this year.

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