diff --git a/engine/match.go b/engine/match.go
index df43b50..8b8ab5f 100644
--- a/engine/match.go
+++ b/engine/match.go
@@ -111,6 +111,10 @@ func (mr *MatchRunner) Run() (*MatchResult, *Replay, error) {
 	// Record initial map state
 	replayWriter.SetMap(gs)
 
+	// Collect state snapshots for win probability computation
+	snapshots := make([]*GameState, 0, mr.config.MaxTurns+1)
+	snapshots = append(snapshots, gs.Clone())
+
 	// Record turn 0 (initial state, no debug yet)
 	replayWriter.RecordTurn(gs, nil)
 
@@ -151,6 +155,9 @@ func (mr *MatchRunner) Run() (*MatchResult, *Replay, error) {
 		// Record turn state with debug
 		replayWriter.RecordTurn(gs, debug)
 
+		// Collect state snapshot for win probability
+		snapshots = append(snapshots, gs.Clone())
+
 		if mr.verbose {
 			mr.logger.Printf("Turn %d: %d living bots", gs.Turn, gs.GetLivingBotCount())
 		}
@@ -160,6 +167,10 @@ func (mr *MatchRunner) Run() (*MatchResult, *Replay, error) {
 		}
 	}
 
+	// Compute win probability via Monte Carlo rollout
+	winProbs, criticalMoments := ComputeWinProbability(snapshots, 100, mr.rng)
+	replayWriter.SetWinProbability(winProbs, criticalMoments)
+
 	// Finalize replay
 	replayWriter.Finalize(result)
 
diff --git a/engine/replay.go b/engine/replay.go
index 93fdd63..26b5814 100644
--- a/engine/replay.go
+++ b/engine/replay.go
@@ -9,15 +9,17 @@ import (
 
 // Replay records the complete history of a match for playback.
 type Replay struct {
-	FormatVersion string        `json:"format_version"` // semver, e.g. "1.0"
-	MatchID       string        `json:"match_id"`
-	Config        Config        `json:"config"`
-	StartTime     time.Time     `json:"start_time"`
-	EndTime       time.Time     `json:"end_time"`
-	Result        *MatchResult  `json:"result"`
-	Players       []ReplayPlayer `json:"players"`
-	Map           ReplayMap     `json:"map"`
-	Turns         []ReplayTurn  `json:"turns"`
+	FormatVersion   string            `json:"format_version"` // semver, e.g. "1.0"
+	MatchID         string            `json:"match_id"`
+	Config          Config            `json:"config"`
+	StartTime       time.Time         `json:"start_time"`
+	EndTime         time.Time         `json:"end_time"`
+	Result          *MatchResult      `json:"result"`
+	Players         []ReplayPlayer    `json:"players"`
+	Map             ReplayMap         `json:"map"`
+	Turns           []ReplayTurn      `json:"turns"`
+	WinProb         []WinProbEntry    `json:"win_prob,omitempty"`
+	CriticalMoments []CriticalMoment  `json:"critical_moments,omitempty"`
 }
 
 // ReplayPlayer represents player info in a replay.
@@ -174,6 +176,12 @@ func (rw *ReplayWriter) RecordTurn(gs *GameState, debug map[int]*DebugInfo) {
 	rw.turns = append(rw.turns, turn)
 }
 
+// SetWinProbability sets the win probability data and critical moments on the replay.
+func (rw *ReplayWriter) SetWinProbability(winProb []WinProbEntry, moments []CriticalMoment) {
+	rw.replay.WinProb = winProb
+	rw.replay.CriticalMoments = moments
+}
+
 // Finalize completes the replay with the match result.
 func (rw *ReplayWriter) Finalize(result *MatchResult) {
 	rw.replay.EndTime = time.Now().UTC()
diff --git a/engine/winprob.go b/engine/winprob.go
new file mode 100644
index 0000000..7f5037d
--- /dev/null
+++ b/engine/winprob.go
@@ -0,0 +1,181 @@
+package engine
+
+import (
+	"fmt"
+	"math"
+	"math/rand"
+)
+
+// WinProbEntry holds per-turn win probabilities for each player.
+type WinProbEntry []float64
+
+// CriticalMoment identifies a turn where win probability shifted significantly.
+type CriticalMoment struct {
+	Turn        int     `json:"turn"`
+	Delta       float64 `json:"delta"`
+	Player      int     `json:"player"`
+	Description string  `json:"description"`
+}
+
+// ComputeWinProbability runs Monte Carlo rollouts from each snapshot to estimate
+// per-turn win probability. For each turn T, it clones the state, runs numRollouts
+// random-play rollouts to match end, and computes win_prob[T] = wins[i] / numRollouts.
+func ComputeWinProbability(snapshots []*GameState, numRollouts int, rng *rand.Rand) ([]WinProbEntry, []CriticalMoment) {
+	if len(snapshots) == 0 || numRollouts <= 0 {
+		return nil, nil
+	}
+
+	numPlayers := len(snapshots[0].Players)
+	winProbs := make([]WinProbEntry, len(snapshots))
+
+	for t, snap := range snapshots {
+		wins := make([]int, numPlayers)
+		draws := 0
+
+		for r := 0; r < numRollouts; r++ {
+			clone := snap.Clone()
+			clone.rng = rand.New(rand.NewSource(rng.Int63()))
+			winner := runRandomRollout(clone)
+			if winner >= 0 && winner < numPlayers {
+				wins[winner]++
+			} else {
+				draws++
+			}
+		}
+
+		entry := make(WinProbEntry, numPlayers)
+		for i := 0; i < numPlayers; i++ {
+			entry[i] = float64(wins[i]) / float64(numRollouts)
+		}
+		winProbs[t] = entry
+	}
+
+	criticalMoments := detectCriticalMoments(winProbs, snapshots)
+
+	return winProbs, criticalMoments
+}
+
+// runRandomRollout plays random moves from the given state until the match ends,
+// returning the winner player ID (-1 for draw).
+func runRandomRollout(gs *GameState) int {
+	directions := []Direction{DirNone, DirN, DirE, DirS, DirW}
+
+	for gs.Turn < gs.Config.MaxTurns {
+		gs.ClearTurnState()
+		submitRandomMoves(gs, directions)
+		result := gs.ExecuteTurn()
+		if result != nil {
+			return result.Winner
+		}
+	}
+
+	// Max turns reached — determine winner by score
+	winner := gs.findWinnerByScore()
+	return winner
+}
+
+// submitRandomMoves assigns a random direction to each living bot.
+func submitRandomMoves(gs *GameState, directions []Direction) {
+	for _, b := range gs.Bots {
+		if !b.Alive {
+			continue
+		}
+		dir := directions[gs.rng.Intn(len(directions))]
+		if dir != DirNone {
+			dest := gs.Grid.Move(b.Position, dir)
+			if gs.Grid.IsPassable(dest) {
+				gs.SubmitMove(b.Position, dir)
+			}
+		}
+	}
+}
+
+// detectCriticalMoments finds turns where win probability shifted by more than
+// threshold for any player. It uses events from the game state snapshots to
+// generate human-readable descriptions.
+func detectCriticalMoments(winProbs []WinProbEntry, snapshots []*GameState) []CriticalMoment {
+	const threshold = 0.15
+
+	var moments []CriticalMoment
+
+	for t := 1; t < len(winProbs); t++ {
+		prev := winProbs[t-1]
+		curr := winProbs[t]
+
+		for player := 0; player < len(curr); player++ {
+			delta := curr[player] - prev[player]
+			if math.Abs(delta) >= threshold {
+				desc := describeCriticalTurn(snapshots, t, player, delta)
+				moments = append(moments, CriticalMoment{
+					Turn:        t,
+					Delta:       math.Round(delta*100) / 100,
+					Player:      player,
+					Description: desc,
+				})
+			}
+		}
+	}
+
+	return moments
+}
+
+// describeCriticalTurn generates a template-based description of why a turn was critical.
+func describeCriticalTurn(snapshots []*GameState, turn int, player int, delta float64) string {
+	if turn >= len(snapshots) {
+		return fmt.Sprintf("Player %d win probability %s to %.0f%%", player, direction(delta), math.Round(math.Abs(delta)*100))
+	}
+
+	snap := snapshots[turn]
+
+	// Count events for this player
+	var combatDeaths, captures, botDied int
+	for _, ev := range snap.Events {
+		switch ev.Type {
+		case EventCombatDeath:
+			if details, ok := ev.Details.(map[string]interface{}); ok {
+				if owner, ok := details["owner"].(int); ok && owner == player {
+					combatDeaths++
+				}
+			}
+		case EventBotDied:
+			if details, ok := ev.Details.(map[string]interface{}); ok {
+				if owner, ok := details["owner"].(int); ok && owner == player {
+					botDied++
+				}
+			}
+		case EventCoreCaptured:
+			if details, ok := ev.Details.(map[string]interface{}); ok {
+				if newOwner, ok := details["new_owner"].(int); ok {
+					if newOwner == player {
+						captures++
+					}
+				}
+			}
+		}
+	}
+
+	switch {
+	case combatDeaths > 0 && delta < 0:
+		return fmt.Sprintf("Player %d loses %d unit(s) in combat, win probability %s to %.0f%%",
+			player, combatDeaths, direction(delta), math.Round(math.Abs(delta)*100))
+	case combatDeaths > 0 && delta > 0:
+		return fmt.Sprintf("Player %d wins engagement eliminating %d enemy unit(s), win probability %s to %.0f%%",
+			player, combatDeaths, direction(delta), math.Round(math.Abs(delta)*100))
+	case captures > 0:
+		return fmt.Sprintf("Player %d captures a core, win probability %s to %.0f%%",
+			player, direction(delta), math.Round(math.Abs(delta)*100))
+	case botDied > 0 && delta < 0:
+		return fmt.Sprintf("Player %d loses %d unit(s), win probability %s to %.0f%%",
+			player, botDied, direction(delta), math.Round(math.Abs(delta)*100))
+	default:
+		return fmt.Sprintf("Player %d win probability %s to %.0f%%",
+			player, direction(delta), math.Round(math.Abs(delta)*100))
+	}
+}
+
+func direction(delta float64) string {
+	if delta > 0 {
+		return "rises"
+	}
+	return "drops"
+}