That last encounter was played in the FA Cup third round at the Gills’ Priestfield stadium and was one to forget for the sold out away allocation, who watched Gerald Sibon give them the lead after four minutes before a Marlon King brace and goals for Chris Hope and Guy Ipoua handed the home side a 4-1 win.
An awful lot has changed at both clubs in that time since, but what happened to the players that stepped out in Wednesday colours that day?
Through a raft of switches to Sheffield United, drugs charges and death threats, it’s been an eventful couple of decades for those who were involved.
1. Chris Stringer
A young goalkeeper of some reputation learning his trade alongside Kevin Pressman, Stringer was playing a handful of cup games at this stage but didn't have the best game of his Wednesday career, shipping four goals. Was sadly forced to retire in 2001 with health complications.
Photo: Getty Images
2. Steven Haslam
A committed young defender still in the early stages of his career back in 2003, Haslam played in 143 league matches for Wednesday before stints at Halifax, Bury and Hartlepool. Now of course back at Middlewood Road running the Owls' academy.
Photo: Jamie McDonald
3. Leigh Bromby
Another young defender cutting his teeth, Bromby played over 100 times for the Owls across six years before shifting over to the dark side at Bramall Lane. Enjoyed a season at Watford and then some time at Leeds before retiring in 2013. Now acts as head of football operations at Huddersfield Town.
Photo: Julian Herbert
4. Ashley Westwood
A warts-and-all defender, Ashley Westwood signed from Bradford City in 2000 and spent three years at Hillsborough before moving on to Northampton. From there he became something of a journeyman. Is now a globe-trotting manager, having held posts at Bengaluru FC in India, Penang in Malaysia, AIK in Sweden and now RoundGlass Punjab back in India.
Photo: Phil Cole