Cristiano Ronaldo and Kaka were bought during the summer, but even the season before that saw times where the Dutch winger was left out of the starting XI. Robben started just 25 La Liga games in 2008-09, but still was hopeful he could remain in Madrid and fight for his place in the team.
"I didn't want to go but the club wanted to sell me," Robben said following his transfer to Bayern. "There have been many lies but, at the end of the day, I have to decide what's best for me, because I want to play and to show the footballer I am."
Fast forward 10 years and Bayern find themselves chasing a talented winger in a similar situation.
Leroy Sane is no longer a guaranteed starter at Manchester City and although the English champions have not added any new attacking talent this summer, the purchase of Riyad Mahrez just over 12 months ago created even more competition on the wings at the Etihad.
Sane started 21 Premier League games last season, down from 27 in 2017-18. Now 23, his career should be projecting upwards. He should be becoming more integral to his club but instead finds his game time lessening under Pep Guardiola.
The Catalan is keen to keep the Germany international at City but that desire always seems to come with a caveat when he is asked about Sane's future.
"He is a guy we appreciate, I like him a lot. I think he can be better," Guardiola told reporters a fortnight ago. "Two times, three times I have said that we want him to stay. That's why he has an offer to extend his contract.
"It's not in our hands. The agreement is good and if he wants to leave, I'll be sad. Hopefully, he stays."
Just two weeks earlier, Guardiola admitted that he only wanted happy players at City but that it could be difficult to keep his entire squad in good spirits when they're not playing every week or starting every game.
"The club made him an offer last year, as I said many times," he said. "We want people here to be happy. We are going to help him to be the best, we know his potential and what his level is. He has a special quality difficult to find around the world.
"He knows, they all know, it’s difficult because of the quality we have. But, at the same time, I spoke to the club 10 times I want people here to be happy. If they are not, they go. The desire to have him to be with us is always there."
Guardiola's comments contrast sharply with those of Bayern head coach Niko Kovac as well as Sane's potential team-mates in Munich, who always speak of the 23-year-old in glowing terms.
"Our club management is very committed [to signing him]. It is not easy in this day and age, you see, otherwise it would already be sorted. But I am very confident. I assume we can get it [done]."
With Robben retired and fellow veteran winger Franck Ribery out of contract, Bayern are eager to add another option to a wide corps which currently only features Serge Gnabry, Kingsley Coman and Alphonso Davies.
If he should arrive at the Allianz Arena, Sane would immediately become the star attraction on the flanks, the man entrusted with most responsibility in terms of creating goals for prolific striker Robert Lewandowski.
The Pole also commented on a potential transfer, saying that Sane's international team-mates are excited by the prospect of also linking up at club level: "Bayern's German players are now very much looking forward to Sane's signing, but we have to wait and see what is going on."
Leon Goretzka has taken up the poaching cause for Bayern, commenting on Sane's Instagram photos with the club motto "Mia san mia". The slogan is Bavarian for "We are who we are" and represents the winning mentality required from the club's players.
"Our bosses have shown him a clear plan. We are very focused, Leroy knows what to expect here, and when a player with such capacity comes to FC Bayern, he knows his job," Kovac told Sport Bild.
"You can see that the transfer is not easy. But I know that our people are working very hard to make it happen. We will do everything to realise this transfer. We all know that Leroy Sane is our dream player. The public knows that, we know that."
Sane is driven to succeed and that is why he has considered leaving back-to-back Premier League champions Manchester City.
He will win plenty of trophies at Bayern too, but most importantly, he will be a first-choice player and get the opportunity to show his football abilities, much like Robben was able to do 10 years ago when he moved from Madrid to Munich.