Actor Anthony LaPaglia celebrates the Hollywood United victory over the Timbers

If you don’t, talk to a Timbers fan who has been supporting the team for a few years.  I bet they will.  If the date doesn’t ring a bell, just ask what the most embarrassing Timbers loss they have ever seen was.  Then they are likely to roll their eyes and remember exactly what happened on that date.

That’s the day Hollywood came to Portland.

As the Timbers prepare to host Cal FC, an amateur team from Southern California, in a US Open Cup match on Wednesday night, many Timbers fans can’t help but remember that rainy night in June four years ago and realize how dangerous a match like this can be.

On that night the Timbers hosted Hollywood United at (then called) PGE Park in a US Open Cup third round match, and though it was a sparse crowd of just over 3,000 that witnessed the match that night, the Timbers fielded a mixture of starters and reserves in what was expected to be an easy romp over a group of amateurs.  As it happened, the Timbers were in for more than they expected and it was a former Timber, Matt Taylor, who punished the Timbers by converting two penalty kicks, this being especially frustrating since the Timbers had missed a penalty of their own that would have put them up 3-1.

Chris Brown fights off the marking of Nas Koubouras

Many Timbers fans also recalled that the same Matt Taylor had missed a couple of sitters the previous September that would have sent the Timbers through to the final that year.

Instead the Timbers would give up two late goals after Takayuki Suzuki missed the penalty chance, and would fall 3-2 in front of a shocked Portland crowd, and the loss would be a source of endless mocking to Timbers fans for years, and continues to this day.

In terms of Timbers losses over the years it might not have been the most painful, especially since the Timbers do have a bit of a reputation for not taking the US Open Cup very seriously.  But it certainly was the most embarrassing, by far.

Tayayuki Suzuki fails to convert a key penalty kick

There is also a celebrity factor in this match, just as there was in 2008 when it was actor Anthony LaPaglia who owned the Hollywood United side, and famously celebrated the win on the pitch afterwards.  This time, it’s former US National Team and MLS star Eric Wynalda who coaches Cal FC, and also just like in 2008, there will be a Timbers alum on the opposing side, as former Timber Mike Randolph will be wearing the opposing jersey.  Oddly enough, the Cal FC kits are old Chicago Fire jerseys right down to the “Best Buy” sponsorship, and MLS patch still on the shoulder.

But that’s not to say that Cal FC is just a bunch of amateurs wearing MLS surplus jerseys.  The USASA side has already beaten the PDL Champion Kitsap Pumas and USL Pro Division Wilmington Hammerheads on the road, the most recent result a 4-0 pounding of the Hammerheads in North Carolina.

Justin Thompson attempts a header against Hollywood United

No Timbers players remain on the roster who were on the Timbers roster that night, but plenty of the fans in the stands will remember that June night in 2008 when the Timbers found out exactly how embarrassing it is to lose to an amateur side at home, and on the Timbers sideline and within the Timbers organiztion, there will still be the memories of that 3-2 loss four years ago to remind them exactly what can happen if you underestimate any opponent, no matter how much of a mismatch you think it might be. match report of Hollywood United match:

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