Arsenal's quest for a first trophy since 2005 suffered another blow last night when they were beaten on penalties by npower League Two Bradford at Valley Parade in the quarter-finals of the Capital One Cup.
After guiding Arsenal to earlier great success, Wenger's plans to build a team capable of sustaining a challenge for honours were shattered by the departures of Samir Nasri, Cesc Fabregas, Robin van Persie and Alex Song.
In a wide-ranging interview with the January edition of Four Four Two magazine, conducted before yesterday's loss at Bradford, Wenger admits there will always be a sense of what might have been if the club had been able to retain their talent.
"My regret is that we already had a great team two or three years ago which could compete on four fronts," Wenger said.
"We just missed out in the Champions League [last 16 tie] against Barcelona, when we could have scored in the last minute, and then we just missed out on the Premier League too.
"But you could feel the potential was there, and I thought, 'Okay, let's do this together'. Then the team split up, sometimes after five or six years' work, it is frustrating, you have to start all over again."
Wenger added: "We have lost recent players earlier in their careers - to lose Van Persie, Fabregas, Nasri and Song in just two years, it is a massive amount of potential, of course you worry."
Following Arsenal's decision to leave Highbury in 2006 for the 60,000-seater Emirates Stadium, the north London club found themselves having to battle the financial commitments to the move as well as the seemingly bottomless pockets of rivals including Manchester City and Chelsea.
Wenger turned 63 in October and his position has come under increasing scrutiny this season.
The Frenchman, whose contract runs until June 2014, feels he must remain true to the values he inherited when taking over more than a decade ago.
He said: "I am not saying I never made mistakes. I was fortunate to work for this club for 16 years and I hope I respected the traditions of this club. I feel fortunate, but I think somewhere as well I tried at least pay the club back with the trust they had in me."
Arsenal have long championed their self-sustaining business model.
Chief executive Ivan Gazidis maintains it is a philosophy which will give Arsenal an edge on the pitch, with UEFA's financial fair play regulations soon to kick in.
"Let's be clear - we don't see Champions League qualification as enough, we are proud of our record, but we want to do more, and we will," Gazidis told Four Four Two.
"Irrespective of financial fair play's impact, we will be among the top five most financially powerful clubs in the world by 2014, that is when we will really start competing."