The Manchester United executive vice-chairman had grand plans to bring the pair to Old Trafford in 2013 as he sought to kickstart the post-Sir Alex Ferguson era with a bang.
Yet, as it transpires, the farcical summer window under David Moyes left the club further behind bitter rivals Man City and Liverpool than ever before in the Premier League era.
Former United assistant manager Mike Phelan alluded to a complete change of position for Woodward at United at this time; no longer was he in charge of bringing money to the club and driving commercial opportunities, he was also in charge of spending.
United started the summer by making the all the right noises - they wanted to spend and spend big - Moyes even spoke of an unlimited budget.
Indeed, Woodward himself suggested 'there was no cut-off price' and that the club would back Moyes to the hilt in pursuit of 'stellar' players.
But by the end of the window, the club were reduced to little more than a laughing stock after what many media outlets described as a 'farcical' transfer window amid claims of Spanish imposters and incomplete paperwork.
So who exactly were United linked with, how close where they to signing them and why did it all go so horribly wrong?
There was a time when the Portuguese superstar being linked with a return to Old Trafford was as certain as rain during British summertime.
After leaving Old Trafford for Real Madrid in 2009, the world's most expensive player continued to be linked with a sentimental return to the club he spent six years establishing himself as the best in the world.
Moyes refused to rule out a move for Ronaldo in 2013, but (despite exploring all possible avenues to bring him back) it was nothing more than a pipe dream.
"Sir Alex [Ferguson] had told me there was always a chance Ronaldo might come back from Real Madrid," Moyes mused in 2016. Optimistic, to say the least.
The Liverpool midfielder made a glittering debut on Sunday at Stamford Bridge and managed to break a Premier League record in just 45 minutes.
But it could have been the red of Manchester United the Spain international donned instead, with Moyes pulling the plug on a deal to bring the former Barcelona midfielder to Old Trafford.
Sir Alex Ferguson was desperate to sign the precocious talent following his performances at the Under-21 European Championship in 2011, but was forced to wait a couple of years to make it happen.
Yet despite practically handing the midfielder to Moyes on a silver platter, the former Everton boss decided to back away from the deal as he was not convinced.
During the Sydney leg of United's pre-season tour, Moyes confirmed his interest and a firm offer for the Barcelona midfielder.
In fact, the Spaniard was one of the first names on his wish list after leaving Everton: "The other one I came really close to getting was Cesc Fabregas, who we thought we would get [from Barcelona] right up until the last minute.
"The Cesc one was disappointing, it was very close."
Woodward headed home from Sydney to resolve the situation surrounding Wayne Rooney and close a deal for Fabregas, but three bids were rejected. He then gave a press conference to the Catalan press stating he had never wanted to leave, with reports in Europe suggesting Woodward was out of his depth.
When Woodward mentioned the seemingly limitless funds for 'stellar' players, it was a phrase meant with Gareth Bale in mind.
After a stunning season with Tottenham Hotspur in 2012/13, the Wales international seemed destined for a massive club and United and Moyes were desperate to sign him.
"When I first went in to United my real target was Gareth Bale," Moyes told the Guardian in 2016.
"I felt all along that Gareth Bale was a Manchester United player and I fought to get him [from Tottenham] right up until the last minute. We actually offered him a bigger deal than Real Madrid but Gareth had his mind made up on going to Madrid. He was, though, in my mind, the player I really wanted."
Although this move may seem like a bullet dodged in hindsight, the World Cup winner was one of the most coveted players in the world in 2013 after it transpired Real Madrid wanted rid of him.
The Daily Mail confirmed United made two deadline day bids for Ozil once they learned of Arsenal's interest in the player, while a source told the MEN that Moyes was desperate for a deal to be struck.
"United made a call," the source claimed. "Kenny Moyes, David's brother who is an agent, was trying desperately to get hold of Ozil's agent.
"I think that by the time they managed it it was too late."
The former Real Madrid left-back was seen as an alternative option to Leighton Baines, a player Moyes wanted to join him from Goodison Park at the same time as Marouane Fellaini.
Everton did not want to sanction a joint deal - something which was finally accepted on deadline day 2013 - with United only offering £15m for Baines when the Toffees politely told then £20m or forget it.
Moyes tried desperately to bring the 25-year-old Portugal international to Old Trafford on loan, but the deal fell through.
United submitted their share of the paperwork on time, but Real's move for Guilherme Siqueira from Granada as a replacement also collapsed after he chose to join Benfica and United were left with nothing.
How Manchester United could have looked in 2013?
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You would forgive Ed Wooward if the sight of Thiago Alcantara leading Chelsea a merry dance and Gareth Bale posing with his new Tottenham Hotspur shirt made him somewhat nauseous.