Gareth Bale is another possible departure, but is a lot less likely to try and force through a move. We tend to forget he's still just 22. Still a relative youngster with, injury permitting, a solid thirteen or fourteen years left in the tank.
But I've said before that he, and other first choice winger Aaron Lennon, need some competition. In a perfect world, Harry would have properly utilised Stephen Pienaar and Niko Kranjcar's talents, and to some degree, Andros Townsend's and we wouldn't have to worry about this. But he didn't.
Kranjcar is a favourite of mine. Enough to get his name and number on the back of my Investec home shirt this season. Which was just as well as his best performances were saved for the cup competitions, notably the third round of the FA Cup against Cheltenham at White Hart Lane. And who played alongside him that day? Mr Pienaar.
Both are similar players, most at home cutting in from the left wing on to their favoured foot and adding a creative spark. Pienaar was shipped back off to Everton in January, a move questioned by the majority of the Spurs community, which left us very short of midfield cover.
His signing was an odd one, wreaking of Daniel Levy's joy at buying a proven Premier League player on the cheap, with the potential to make a profit on him. Kranjcar, similar player as I've said, was already at the club, and was already hardly getting a look in. Despite a recent showing when he came off the bench in consecutive games to score the winning goal.
We did look like we had got value for our money though on that glorious night at the San Siro, when AC Milan were dispatched 1-0 and Pienaar worked tirelessly down the left wing in place of the returning from injury Gareth Bale.
Pienaar is said to be keen on making his loan to Everton permanent after not enjoying his time in London. It's worth noting the significant improvement in the South Africans form since returning to Merseyside, playing the sort of football Spurs could have benefitted from during our sticky patch from February onwards.
I can't see Pienaar being a Spurs player next season and there will again be doubts over Kranjcars future. Young winger Andros Townsend, who impressed on loan at Birmingham City in the latter stages of the season, is another who has featured on both wings for Tottenham.
His pace and ability to cross without breaking stride have drawn comparisons with Bale, while his versatility has seen some call for his inclusion in our squad. He showed in glimpses during our half-hearted Europa League campaign of his potential, as well as with a man of the match performance against Charlton Athletic in the FA Cup in January 2011.
He is likely to feature heavily again in next seasons Europa League, though hopefully not at left back, or experience another loan spell. The latter is the best option in my opinion, hopefully a loan with a Premier League team, much in the same way Steven Caulker did this season.
This way we could quickly discover if he is capable of playing at a higher level, or whether he will ultimately be deemed not good enough.
David Bentley is likely to be shown the door again, whether permanently or on loan because no one is willing to take a risk on a player whose career has stagnated. I had hoped he still had a part to play, given that he's a Spurs fan, but given Harry's reluctance to show any faith in him has all but sealed his fate.
Strengthening is a priority in my eyes. Ideally, we want someone who is versatile, with pace, and that won't just be joining as back up, but as serious competition. Though that will of course depend on Harry's willingness to rotate next season, something we all know we suffered from a lack of this season.
He's been touted by plenty already, but I'm very keen for us to sign up Junior Hoilett from recently relegated Blackburn Rovers. The Canadian attacker is out of contract next month and is already comfortable in the Premier League in a variety of positions.
This season alone he has played on both the left and right wings, often with a licence to roam, and behind the main striker. Straight away you have cover/competition for Bale, Lennon and van der Vaart with just one signing.
He has pace to burn, ability to beat a man and a lethal shot. I was at Ewood Park this season to witness our 2-1 victory and Hoilett really stood out. Those around me collectively gulped any time he picked up the ball and started running at our fragile defence. One of his biggest assets is the questions he poses for a defender when running at them due to his ability to beat him on the outside or cut back inside. This causes defenders to second guess and often leave themselves wide open to one or the other.
Similar to Demba Ba's transfer to Newcastle, on a Bosman, the deal offers little in the way of risk, an attraction no doubt to Mr Levy, as well as the possibility of a hefty sell on fee. He's proven in the league, and still has bags of potential.
It's a move already picked up by the papers, but the Canadian international has had plenty of admiring glances this season and is likely to look for the best financial package, as well as a guarantee of first team football, before deciding where his football future lies.
Hopefully, it'll be at White Hart Lane.
“It is better to fail aiming high than succeeding aiming low. And we at Spurs have set our sights very high, so high in fact that even failure will have in it an echo of glory” Bill Nicholson.