Richard raised a company of archers to fight at the battle of Flodden in 1513 from Middleton, near Manchester. An heraldic visitation in 1533 by Clarenceux King of ArmsThomas Benolt noted that Richard had captured the courtierJohn Forman, sergeant porter to James IV of Scotland and Alexander Burnett, Sheriff of Aberdeen, at Flodden. John Forman was taken to Berwick upon Tweed where he identified the body of James IV of Scotland. Richard continued the rebuilding the parish church of St. Leonard's at Middleton. He commissioned the "Flodden Windows" depicting himself and his wife, and seventeen captains of the archers, and the priest Henry Taylor who blessed them before the battle, commemorating them each by name in stained glass. The windows are one of the oldest war memorials in England, second in date to All Souls College, Oxford, founded in 1438 with the provision that its fellows should pray for those killed in the French wars. The main inscription on the glass was, as described in 1845; "Orate pro bono statu Richardi Assheton et eorum qui hanc fenestra fieri fecerunt quoru noina et imagines ut supra ostendatur. Anno dni, MCCCCCV", meaning "Pray for the wellbeing of Richard Assheton and those whose names and images they caused to be made in the window shown above, 1515." As there was no "X" in the painted date, it has been argued that the window dates from the decade before Flodden, and commemorates a religious confraternity of archers. The legible names included; Henricus Taylyer, Richard Kylw, Hughe Chetham, James Gerrarde, John Pylkyngton, Philipe Werburton, William le, John Scolefede, Wylliam, James Taylier, Roger Blomeley, Crystofer Smythe, Henry Whitaker, Robart Prestwyche, and Richard Bexwicke. The window is described in a 17th-century poem Iter Lancastrense by Richard James, c.1636;
Now go we to the church of Middleton To find out there some glory of our own At charge of those good men who went out far In suite of brave Ashton to the warre There stands a painted window, where I weene The show of their departure may be seene The Lord and Ladye first in skarlett; then One neere attending of ye chiefest men Their garments long, his short and bliew, behinde The chaplaine of ye warfare you may finde In robe of ye same colour, for to say Before an altar praiers of ye daye On bended knees; him follow neighbours bould Whoe doe bent bowes on their left shoulders hould Their girdle sheaft with arrowes; as the squire So are they all, court mantells in attire Of blewe; like Greeks in Trojan warre, their haire In curles long dangling makes ye semblance faire And sterne; each hath his name, and people tell That on ye same lands now their children dwell As yet so called.
Originally there was more than one window, with Richard and his wife shown separately, since 1847 the remaining glass forms one window. The window was restored again in 2012.
Family
Richard married Anne Foulshurst, daughter of Sir Robert Foulshurst of Crewe, their son was Richard Assheton of Middleton who married firstly Anne Strickland, and secondly Anne Lady Bellingham. The Asshetons of Great Lever, Lancashire were Richard's cousins. Two were members of parliament; Richard Assheton of Whalley and Downham, Lancashire, and his half brother Ralph Assheton of Great Lever at Middleton, who was Member of Parliament for Liverpool in 1553.