The Owls face the U's in the first round of the League Cup.
Trevor Benjamin's goal knocks Wednesday out of the 1998-99 edition
Not only is it nearly 20 years since the two teams' last meeting - a 1-1 draw which was enough to send the then-fourth-tier U's through to round two 2-1 on aggregate - a familiar face is in line to feature against the Owls for the very first time.
It's nine years since Barry Corr left Hillsborough for Swindon Town, and the fact that, for as bad as Wednesday have been since then, their paths are yet to cross, speaks volumes of the challenge he faced in Sheffield.
Corr struggled to make an impact at Hillsborough
Corr arrived ahead of the Owls' initial promotion back to the Championship in 2005, following his release by Leeds United.
And as a 20-year-old with no prior first team experience, the young Irishman found the going incredibly tough - despite the almost unconditional love shown to him by Paul Sturrock, Wednesday's manager at the time.
Injuries certainly played a part, restricting him to just 18 appearances during his first season in blue and white, with only nine of those starts. Still, no goals arrived.
Sturrock always had faith in Corr's ability
Corr's final outing came the following September, when having squandered a one-goal lead against ten-man Derby County, he was thrown on by Sturrock with six minutes remaining. Paul Peschisolido's stoppage time winner for the Rams remains the only thing which, in 20 years of attending football matches, has prompted me to leave one early.
Sturrock persevered, though, and reunited with Corr four years later at Southend Uniited, where the striker, to his credit, spent five largely productive campaigns before joining the U's last summer.
And his 65 goals in 185 League Two games suggest to me two things: One, this was always Corr's level. And two, he may just be capable of imparting one final, truly awful memory on the supporters of Sheffield Wednesday.
Corr has proved a handful in England's bottom tier