The Dutch star, now plying her trade with Fiorentina, will face some of her old teammates on Wednesday, as the two sides lock horns in the Women’s Champions League Round of 16.
The 28-year-old will step out onto her former home turf once again before City travel to Italy the following week.
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Middag – a fans’ favourite on and off the pitch during her time in Manchester – says she knew the pair would be pitted together in the draw and was thrilled by the prospect.
"I was really happy! I felt like it was going to happen!” she told ManCity.com.
"I was at my teammate's house and the first part of the draw had been made and we were like: 'Here we go! This is our part!'
“The first team that came out was 'Manchester City' and we knew there was a good chance because of the groups...
"I thought: 'Surely, it must be Fiorentina!' and there it was! I was very happy.
“Especially given the situation with COVID-19, you are not able to travel as much so I'm happy that by drawing City, I can return to the city where I enjoyed living for two years. Although I will not be able to explore, it will be good to go back.
"After the draw, I text Steph Houghton and Karen Bardsley and I'm looking forward to seeing the girls and the staff.
“There have been a lot of changes since I played there but I still know people like Alan Mahon- or 'Mahony'! - and the goalkeeping coach Chris Williams. I knew Gareth Taylor a little too from his time as Academy Coach and he's doing a good job.
"City are in great form at the moment so it's a tough opponent for us to play against!"
A mid-season signing in the summer of 2016, Middag won two trophies in her first four months at the Club – a league and cup double!
However, her City career was sadly hampered by a ten-month cruciate ligament injury.
Any player would be forgiven for looking back on such a difficult period with sadness – but Middag says she has nothing but fond memories of her time in Manchester.
"It's down to the people that make the Club and the city,” she explained. “To me, it really felt like a close-knit community and the people were so nice.
"Of course, from a football point of view, I would have liked to have shown the fans a bit more of what I could do and prove myself... but not many players get the opportunity to play for such a big club.
"My injury did affect what I could do on the pitch but from a human perspective, I'm happy with the connections I made there. I still have very warm feelings about Manchester as a whole and City as a Club.
"Winning three trophies was quite a highlight!
"I joined in the middle of the season and then pretty soon, I already had two trophies on my CV! I remember my teammates at Ajax were joking that I would need a new cabinet for all of the trophies if it continued!
"There were so many good memories... the football we played, the facilities, playing in front of the fans and also having my parents and sister in the stand... It was an incredible time.
“I remember the first day after I signed, I was almost like a little girl in a candy store!
"I was really impressed by everything - the facilities, the quality of the training sessions, the energy in the team, the kindness of the girls...
"Because we shared the training ground with the men, I remember bumping into Vincent Kompany in my first week in Manchester. We were speaking Dutch together and I was thinking: 'This is incredible! Where am I?!'
"From all perspectives, it was really enjoyable."
Hear more from Tessel in an in-depth Q&A in Wednesday’s matchday programme, as she tells us about life in Italy, her new club, her favourite City memories and more…