David Bentley probably never thought he would hit a better shot this season than his 40 yarder against Arsenal last October.
But Tottenham midfielder Bentley has surpassed himself and won a £15,000 Hublot watch in the process.
Bentley challenged his agent Rob Segal of kicking a ball off the roof of the Red Bull headquarters in central London to see if he could get it straight in a skip in the street below.
It has not only been a huge hit on YouTube but has given Bentley reason to smile in an otherwise pretty depressing season since his £15m move to White Hart Lane last summer.
Bentley is far from being his normal self and his mischievous smile has gone but returns briefly when thinking about his charity challenge.
"We were just messing around on the roof of the Red Bull building, with some of my friends that work there and I just decided to have a bet over Rob's watch," said Bentley.
"People have watched it on YouTube and didn't believe it was done. But I did it. Rob was stunned but gave me the watch and we both came to the decision to donate it to charity.
"We'll come up with a good charity. That'll be the best thing for it. It was a good laugh and lots of people have been asking me about it." Bentley is the first to admit that his season otherwise has left him depressed after struggling to live up to the expectations that go with a big price tag as Spurs season has lurched from disaster to disaster.
It has been an awful season at White Hart Lane. Juande Ramos was sacked, they are still in relegation trouble and their UEFA Cup campaign is in danger after their defeat at Shakhtar Donetsk last Thursday.
The one bright spot is next Sunday's Carling Cup final against Manchester United at Wembley and Bentley is determined to finish on a high, although Redknapp has indicated he is still finalising his midfield.
Bentley admits that this season has left him very low at times even though he still enjoys springing a surprise on long-suffering Tottenham fans whenever he sees one wearing a shirt with his name on it.
"Every time I see a Bentley shirt, I pull over and say: 'do you want me to sign that?' I've done that a few times," smiles Bentley, a self-confessed Tottenham fan.
"That's brilliant when I do that, absolute quality. But I'm either very high or low.
"When you first come into the club, expectations and things haven't worked out like that. It has been difficult but hopefully I have put the difficult times behind me and can move on.
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"It's been difficult. I wanted to come to a club that was growing and going in the right direction. But it hasn't panned out like that.
"The fans are going to get on your back because they expect a lot, they want a lot and it is difficult to take. But from now until the end of the season, I want to put a few things right." Bentley has done a lot of soul searching in the past few months and has taken Tottenham's poor form harder than most and still struggles to find answers when the club has such a strong squad.
"Sometimes in football you have to think with your head rather than your heart," said Bentley. "If you wear your heart on your sleeve then football is not a business where you can do that. It's very difficult.
"You become emotionally attached to things and you end up suffering because of it. I'm going to try and think with my head rather than my heart a bit more.
"We're trying to find a way of playing. We're trying to find a formula that will work for everyone - the club, the fans and the players. That's what we're trying to do.
"If we can find that sort of consistency then we can go far. Individually all of the players are brilliant, everything's in place but it's just a few things that have to be put right.
"But a football club has to have a heart and soul. It can't just be build on financial. Just because you have big players it doesn't mean anything. Hopefully that's what we'll do.
"It's difficult for a player to understand, too. You look around the dressing room, see so many good players and you say: 'well, what's wrong?'" Bentley still believes that Tottenham can finish on a high by winning the Carling Cup after overcoming a topsy turvy semi final with Burnley.
"The whole thing was strange but that was Tottenham's season all over and the life I've had at the club so far was all in that game. That just sums it up. What went on was just incredible," said Bentley.
"We're trying to iron out those mistakes and build on that. I don't think we went into the second leg with a bad mentality.
"They had a few opportunities, put them in the back of the net and that's the way it's gone for us. We all go out there with the right mentality but maybe we're even trying too hard at the moment.
"We got there in the end and you learn a lot about yourself from difficult experiences. If you can come through it together it's better for the team and for the club.
"I watched last year's final. I enjoyed it, it was good. Anyone going into a game with Manchester United is going to start as underdogs. That game will be a difficult game but we're more than capable of winning it.
"People remember cup finals and if we stay in the league, win the cup then hopefully they will forget the bad and the ugly stuff that's gone on this season."
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