Manchester City were intent on a strong summer transfer window in 2017 but did not get everyone they wanted after dealing with Arsenal

One of the biggest red flags for Pep Guardiola in his first season in charge of Manchester City came at Monaco. Their form had been too inconsistent to challenge for the Premier League against Antonio Conte’s relentless Chelsea side but there were still faint hopes of European glory in the hands of a man whose worst Champions League finish was a semi-final exit.

City were favourites as they headed to Monaco for the second leg of their last-16 clash after a football feast at the Etihad ended in a 5-3 win. All the Blues had to do was protect their two-goal lead and they would be through.

Except, this being Guardiola, his idea of protecting the lead was to take the game to Monaco and impose their football on their opponents to see out the game. This felt uncomfortable for many in the City team when first thoughts for defending a two-goal lead were to defend.

In the end, they did neither and lost 3-1 to go out on away goals. That game helped to cement Guardiola’s belief that huge changes were needed in the summer of 2017.

They came, with no small help from Monaco. Bernardo Silva and Benjamin Mendy arrived at the Etihad for close to £100 as part of a dismantling of the Ligue 1 champions that totalled nearly £300m; Kylian Mbappe was the headline sale, although most of the money would come from the Premier League and help transform that league.

City spent more than £200m in total that summer but were willing to go closer to £300m as deadline day approached. They had made clear all summer that they were interested in signing Alexis Sanchez from Arsenal, and pushed hard in the final hours to get the job done.

The interest in Sanchez had already had repercussions, with one of the club’s most talented youngsters seeing that move as a sign that he needed to move. It’s intriguing to think what might have happened if Jadon Sancho had stayed at the Etihad, but he was instead sold to Dortmund for £8m and his career took a very different turn.

City finally had a £60m offer for Sanchez accepted by Arsenal, but only on the condition that they could sign a replacement. They headed back to every club’s favourite shop that summer and offered Monaco £92m for Thomas Lemar.

It was happily accepted to put in motion more dizzying transfer activity – until the player himself stopped it. Lemar had been courted by plenty of clubs that summer and was holding out for a move to Liverpool.

With hours left in the window, City had to accept defeat. There wasn’t enough time for Arsenal to convince an unwilling Lemar to sign for them so they would have to abandon plans to sign Sanchez – for now.

The Chilean only had a year left on his contract so City maintained an interest, but that famously would be gazumped by a hungry and splurging United. Sanchez instead sums up the waste of talent at Old Trafford since Sir Alex Ferguson’s retirement with his most iconic moment at the club being a signing announcement involvement that will still make you wince so hard you will want to swallow your hand.

As well as Sancho being an indirect part of the failed move for Sanchez, Raheem Sterling ended up becoming the headline news from it. Guardiola still wanted a finisher and still wasn’t convinced by Sterling for much of that season – Mikel Arteta had to reassure him after a glaring miss at Burnley – but the former Liverpool man turned it round.

By the time he left City in 2022, he had clocked up more goals and assists than anyone who has played for Guardiola other than Lio