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The first ever meeting was a pre-season friendly at Adams Park on 25th July 1995 for Alan Smith's first game in charge of Wanderers at Adams Park. Alex Mathie gave the visitors the lead on nine minutes but Mickey Bell levelled on 24 minutes after being put through by Steve Brown. Desouza then gave Wycombe the lead on 31 minutes when he struck home from the edge of the box following an assist from Steve McGavin. Town, who included 'veteran' John Wark in their side, equalised after the break when Lee Chapman won the ball in the air for Mathie to set up Gus Uhlenbeek for a shot that Paul Hyde got a hand to but couldn't keep out.
Wycombe: Hyde, Cousins, Hardyman, Crossley, Howard, Brown, Carroll, Bell (sub 60 Hemmings), Desouza (sub 71 Garner), McGavin, Soloman - subs not used: Thompson, Clark
Ipswich: Pears (sub HT Tarrico), Yallop, Thompson, Sedgley, Wark, (sub HT Vaughan), Williams, Uhlenbeek, Thompsen (sub 72 Tanner), Mathie, Marshall, (sub HT Chapman), Milton (sub 55 Slater) - subs not used: Wright, Gregory, Mason
All other meetings prior to the Football League meeting on 26th November 2019 were Reserve team fixtures in the Football Combination.
28th October 1998 - a Wycombe team made their first ever trip to Portman Road - Town running out 1-0 winners.
29th March 2000 - Wanderers thrashed 7-0 at Portman Road.
After a break from being opponents in the Football Combination, the two sides then met home and away during the 2008/9 and 2009/10 seasons in what had become the Eastern Division of the Football Combination.
Tues 16 Sep 2008 - Ipswich 3 Wycombe 4
Tues 13 Jan 2009 - Wycombe 2 Ipswich 1
Weds 24 Feb 2010 - Ipswich 1 Wycombe 2
Tues 2 Mar 2010 - Wycombe 1 Ipswich 2
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