AC Milan have been handed a very tricky Champions League qualifying tie says James Horncastle, and with a far from perfect build-up, the Italians could be at the mercy of a free-scoring Dutch side on Tuesday night...
"So with that in mind, perhaps there’s value to be had in backing PSV at 2.89/5 to win on Tuesday and maybe even to qualify at 3.3512/5."
PSV v AC Milan
Live on Sky Sports 1
The draw could have been better for Milan. A lot better. Over at the club's headquarters in via Turati they'd have preferred their Champions League play-off to be against Paços de Ferreira, the surprise package in Portugal last season, who over the summer have lost their manager and a number of players to Porto.
Instead, Milan find themselves travelling to Eindhoven to play PSV on Tuesday night for the first leg of a qualifying tie worth €30m. It's a trap-game for the Italians. Milan have lost on each of their last two visits to the Philips Stadion. One of those defeats, though, felt like a victory.
Down 2-0 in the second leg of their Champions League semi-final in 2005, Massimo Ambrosini scored in the 89th minute to make it 3-2 to Milan on aggregate and book an ill-fated trip to Istanbul. Philip Cocu, who now coaches PSV, got another goal to seal a 3-1 win, but the victory, unfortunately, was pyrrhic. He'll be hoping that this time around things are different.
So what are the chances of that being the case?
Milan are anxious about this game for a number of reasons. Fail to make it through to the Champions League and, without its revenue, they can forget about signing any one of their major transfer targets before the end of the transfer window.
From back to front, a number of players aren't in peak physical condition. Philippe Mexes is only just returning following a series of muscle problems, but it's thought that coach Max Allegri will risk him on the basis that his partnership at centre-back with Cristian Zapata matured towards the end of last season. Milan, incidentally, kept seven clean sheets in their final 12 league games.
Up top, Mario Balotelli isn't 100% either. Remember he suffered a thigh injury before Italy's Confederations Cup semi-final against Brazil, then missed the start of pre-season with a fever before picking up another knock in training ahead of his country's friendly with Argentina last week. That gave Milan a real scare, but it's claimed Balotelli will play, not least because Allegri's options are limited.
Giampaolo Pazzini is still recovering from knee surgery and so, should the going get tough against PSV, they won't be able to go to him and mix it up.
Physical preparation is the issue here. Serie A doesn't start until this coming weekend while the Eredivisie, by contrast, has already been back since August 3. PSV are a couple of weeks into their domestic campaign and top the league after winning all three of their opening games.
It's of great concern for Milan, particularly because they've been slow starters under Allegri. They can't afford for that to happen this time around.
PSV, it must be said, have yet to face a team of Milan's calibre. They also said goodbye to some of their best players over the summer. Kevin Strootman, the future captain of Holland, went to Roma, Dries Mertens left for Napoli, Jeremain Lens joined Dynamo Kyiv and Erik Pieters moved to Stoke, while Mark van Bommel, a member of Milan's last Scudetto winning team two years ago, also retired.
You'd think so many departures would hurt PSV, but so far this young team has demonstrated an exhilarating exuberance. They've scored lots of goals, beating ADO Den Haag 3-2, NEC Nijmegen 5-0 and Go Ahead Eagles 3-0. So with that in mind, perhaps there's value to be had in backing PSV at 2.89/5 to win on Tuesday and maybe even to qualify at 3.3512/5.
Refereeing this encounter is Cuynet Çakir. Manchester United fans will remember him. How could they forget? He sent off Nani in the second leg of their Champions League Round of 16 match against Real Madrid last season, a decision that many felt cost them the game. He has also shown a red card to Balotelli in the past in Manchester City's Europa League clash with Dynamo Kyiv two years ago.
The Sending Off market hasn't fully materialised at the time of writing (2.8615/8 available for small amounts), but when it does look to get matched at around the 3.55/2 mark at least.