Wainwright first played for Yorkshire in 1888, and immediately established his place in the side, chiefly through an innings of 105 against the Australians. He developed slowly over the next couple of years, but his performance on a sticky wicket at Sheffield in 1891 was the performance that established Wainwright as a deadly soft-wicket bowler. Wainwright showed no advancement as a batsman until 1893, when he got close to doing the double and played his first Test at Lord's without success. Wainwright was Yorkshire's leading wicket-taker in 1892, though they fared only modestly, and in 1893, aided by some bad wickets due to a dry spring, he took 90 wickets for 12.55 each, to help Yorkshire win its first Championship. By this time, he and Bobby Peel were the finest slow bowling partnership in county cricket, and they were often unplayable when the wicket helped them.