The Highwaymen will visit National League North club York City knowing a shock win would put them in the first round proper of the competition for the very first time.
The 35-year-old Welshman was forced to retire a couple of years ago after suffering concussion when challenging for an aerial ball in York’s National League North game against Hereford in February 2019.
The 37-year-old has linked up once again with the Minstermen 14 years after his first spell which led to a glittering football career in the Championship with the likes of Birmingham City, Sheffield United and Brentford.
The Tigers have endured significant turmoil in recent seasons, with three consecutive relegations followed in 2019 by the death of CEO Mark Worthington.
Postponements, Covid-19 outbreaks and a protracted wrangle over the termination of the football at Step 2 meant Penn’s side had played just 15 matches by the time the National North campaign was finally voided in February.
The 23-year-old spent a loan spell with the Minstermen during the 2019/20 season and now makes a permanent move to join Steve Watson’s squad after his contract at AFC Fylde expired.
Captain Josh Falkingham slammed in a 76th-minute winner as Town beat National League South Concord Rangers to claim a unique slice of history as the first EFL side to win the competition.