Horseless Headless Horsemann match-ups

Class			Strategy
Scout	vs	Horseless Headless Horsemann	Playing as Scout while being 'It' allows you to dodge the Horsemann's attacks and pursuits due to your agility and ability to double/triple jump. A good idea for a Scout who is "It" is to flee while the Horsemann pursues you away from your team's spawn room. If anything, lure the Horsemann towards the enemy team's spawn room to provide a distraction. Also be aware the Horsemann has a specific search radius around the active control point. It is possible to stop him from chasing you by running away from the control point and evading him until he loses interest in you. This will cause him to attack someone else, or if there is nobody in his search radius, to run back and stand upon the control point to await more victims or to execute a "Boo!" attack.
Soldier	vs	Horseless Headless Horsemann	Rocket jumping over the Horsemann while "IT" will cause him to hesitate while changing directions.It can also keep you well outside of the reach of his attacks, thus giving you the opportunity to either make an escape or draw the Horsemann into a group of enemies. The Buff Banner cannot generate charge by damage to the Horsemann. It is not recommended that you take this to battle with you. Use the Shotgun instead, making the switch to it when you run out of ammo for your primary weapon. This layout allows you to deal the most damage to the Horsemann. As with the Buff Banner the special effect of the Black Box does not work and therefore a considerable drawback when the reduced ammo is taken into account.
Pyro	vs	Horseless Headless Horsemann	Because the Horsemann does not suffer afterburn damage, using the Pyro against the Horseless Headless Horsemann is not recommended. In addition, the short effective range of the Pyro makes attacking head-on a very deadly prospect. However, using the Backburner while he is distracted can be effective in defeating him.
Demoman	vs	Horseless Headless Horsemann	The Demoman can deal a considerable amount of damage to the Horsemann by planting stickybombs where the Horsemann's spawns, before he appears. This would deal a huge amount of damage in an instant. This strategy is particularly effective with a Kritzkrieg charge. As a Demoman, using the Chargin' Targe it is also possible to outrun him by charging repeatedly in a single direction across open ground.
Heavy	vs	Horseless Headless Horsemann	A Heavy/Medic pair should camp the control point where he will spawn next, while building up a Kritzkrieg charge. Then unleash it upon him while he is spawning which subsequently kills him after his spawn animation is complete.
Engineer	vs	Horseless Headless Horsemann	As the Engineer, Sentry Guns will not target the Horsemann. However, you can use the Wrangler to hurt the Horsemann. The Horsemann is not affected by the Sentry Gun's knockback. Also note that the Wrangler's slight auto-aim will not activate, rendering it slightly more difficult to keep the Sentry Gun's fire on-target. Also the Horsemann will attack anything blocking his path, this includes untargeted players and buildings. Keep in mind wrangled Sentry Guns can survive a few hits, allowing you and your team to profit from the distraction.
Medic	vs	Horseless Headless Horsemann	Use your ubercharge on a teammate so they can attack the Horsemann. When the uber wears off run away. If you do not have an ubercharge or Krizkrieg charge run away and build one up.
Sniper	vs	Horseless Headless Horsemann	Both the Sniper Rifle and the Huntsman deal extra damage on headshots against the Horsemann. So stay out of his way and aim for the head. Jarate does not effect the Horsemann so using it or the Sidney Sleeper is ineffective.
Spy	vs	Horseless Headless Horsemann	The Spy is rather ineffective against the Horsemann as a Backstab to the Horsemann will not result in an instant death or a Critical hit and does not contribute significant damage. however The Ambassador deals extra damage on headshots against the Horsemann.