Use your tentacle zones to force Garen into risky (E) spirit pulls and punish his short trades.
Pressure the wave and deny Garen passive healing by controlling the lane with tentacles and (E) threat.
This is a control vs durable side-lane matchup where you want to out-zone and punish his predictable engage pattern.
Trading pattern
Do not chase Garen; let him enter your tentacle zone and punish with (E) followed by (W) and (R) when he commits.
Punish Garen after he uses (Q) silence, as his follow-up damage window is limited.
Avoid extended trades without tentacles, as Garen's short trades and passive healing favor him then.
Danger windows
Be cautious when (Q) silence is up, as it can deny your (E) or (W) and start his short trades.
Avoid fighting outside your tentacle zones where (E) spin and (R) execute can be more threatening.
After (R) is down, ganks become safer for opponents; play around your ultimate cooldown to turn multi-target fights.
Early game
Establish tentacles early around the wave to create safe zones and bait Garen into (E) angles.
Avoid extended fights before level 6; use (E) to trade when Garen commits to short trades.
Use your medium early agency to pressure Garen's passive sustain by forcing him to take poke before he can reset health.
Power spikes
At level 6, (R) creates a major turnaround threat; fight only inside tentacle zones and use (R) when Garen commits.
When you have multiple tentacles and (E) angles set up, your zone becomes hard to contest, forcing Garen to choose between wave control or risking spirit pulls.
Respect Garen's level 6 (R) execute window; avoid low-health trades and reset when his execute is available.
Win conditions
Control tentacle zones to force Garen into unfavorable (E) trades and punish his short trades with (R).
Deny Garen passive healing by pressuring the wave and forcing him to take poke before he can reset.
Reach prepared side-lane states with multiple tentacles to maximize your zone control and turn all-ins with (R).
Tip: For Illaoi vs Garen, read overview, trading pattern, and danger windows first for a fast Top lane check.