Gain on Definition 1 of 3Pro Tip 1/3Physical Proximity Describes decreasing distance, not just physical space but in achievements or goals. She's gaining on the runner ahead. Pro Tip 2/3Competitive Progress Often used in contexts of competition, highlighting progress against others. Our horse is gaining on the frontrunner. Pro Tip 3/3Positive Connotation Implies a good chance of eventually matching or surpassing the one being gained on. You're gaining on the chess champion!