UEFA Champions League: Arsenal v Monaco
Arsenal manager Wenger spent seven years in charge of the Ligue 1 club after taking over in 1987, and Monaco were crowned French champions in his first season at the helm.
Wenger also won the Coupe de France during his successful spell in the Principality before moving on to Japanese club Nagoya Grampus Eight.
The 65-year-old was then appointed by Arsenal in 1996 and is still going strong at the London club, who have being crowned champions of England three times and won the FA Cup five times during his long tenure.
Wenger will come up against injury-hit Monaco for the first time since leaving the club in the first leg on Wednesday and the Arsenal boss admitted he was taken aback when the draw was made.
He told UEFA.com: "To be honest it was a surprise, because I always expect the most prestigious team to come out against us - that has happened the last five or six years.
"It's also one of those strange coincidences in life, because between them these two clubs account for 25 years of my life. That's very unusual, to meet in the Champions League. It was a little bit of an emotional shock."
Arsenal have failed to reached the quarter-finals in each of the last four seasons - losing to Bayern Munich in each of the last two campaigns after Milan and Barcelona also beat them in the round of 16.
Wenger's men moved up to third in the Premier League courtesy of Saturday's 2-1 derby win at Crystal Palace and head into this tie on the back of three consecutive victories.
Monaco should also have a spring in their step after securing a 1-0 derby victory at Nice on Friday despite playing with 10 men for 45 minutes following Aymen Abdennour's dismissal.
That victory - which moved Leonardo Jardim's men up to fourth in Ligue 1 - came at a cost, though, as full-back Layvin Kurzawa suffered a thigh injury and is a doubt for the clash with Arsenal.
Jardim also has concerns over Ricardo Carvalho (calf) and Andrea Raggi (knee), while midfielders Tiemoue Bakayoko (thigh) and Yannick Ferreira Carrasco (knock) also face a race against time to be fit.
Striker Lacina Traore (fractured tibia) is definitely out and captain Jeremy Toulalan misses out due to suspension.
Arsenal, who will have to keep former Tottenham striker Dimitar Berbatov quiet, have concerns over midfielders Alex Oxlade-Chamberlain (groin) and Aaron Ramsey (hamstring).